Ethyl-diisopropyl amine

In the presence of diisopropyl(ethyl)amine, tetrachlorosilane reacts with f-butyl hydroperoxide to give 1 1 adduct 9 (equation 16). Alkylperoxydiorganoalkoxysilanes are prepared from the reaction of chlorodiorganooxysilane with alkyl hydroperoxides in the presence of ammonia or organic base such as pyridine or triethylamine (equations 17 and 18). 

Amino-anilino)-l, 2-diphenyl-cyclopropenylium-tetrafluoroborat [mesomer mit (2-Amino-phenyl)-(l,2-diphenyl-cyclopropenyliden)-ammonium-tetrafluoroborat] cyclisiert beim Ver-such der Deprotonierung mit molaren Mengen an Diisopropyl-ethyl-amin (Hunig-Base) unter Ringspaltung zu 2-[(Z)-l,2-Diphenyl-ethenyl -benzimidazol (89% Schmp. 273-2740)59 (vgl. 

Ohuchida, Hamanaka, and Hayashi (20) have reported a synthesis of the dithia-analogue 21 of tromboxane A. In one of the key steps, the stereoelectroni-cally controlled axial conjugate addition of methyl 3-mercaptopropionate to 68 was realized with stereoselectivity by using diisopropyl ethyl amine (0.2 equiv) in DMF. The product obtained 69, was then converted into 70 which was further transformed into the desired dithio derivative 21 [(a) t-BuoV, HMPA, 25°C (b) NaOCH3, CH3OH (c) NaOH 0.2 N, THF]. 

Cleave the Aloe groups (see Notes 6, 7) Add the resin to 1 g (PPh3)4Pd in 10 mL chloroform acetic aciddV-methyl morpholine (37 2 1, v/v/v) and shake for 5 h. Wash the resin 2x with 25 mL 0.5% diisopropyl ethyl amine in DMF, 2x with 25 mL of 0.5% sodium diethyl dithiocarbamate in DMF, and 2x with 25 mL DMF alone. Special reagents needed tetrakis triphenylphosphine palladium diethyl dithiocarbamate. 

When K2C03 or CsC03 was used as base in acetonitrile, the desired azetidine was isolated in 85-92% yield. The use of 8equiv of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base in dichloromethane at room temperature gave excellent results (90-96%, yield), whereas TEA or diisopropyl ethyl amine (DIEA) gave poor yields (5-25%). Several substituted diazetidines were synthesized (Equation 28). Use of the corresponding optically pure hydrazines 219 afforded chiral diazetidines <2006TL6835>. 

AIBN = 2,2 -azobisisobutyronitrile 9-BBN = 9-borabicyclo [3.3.1]nonane Bn = benzyl BOC = f-butoxycarbonyl Bz = benzoyl CAN = ceric anunoninm nitrate Cp = cyclopenta-dienyl Cy = cyclohexyl DAST = diethylaminosnllur trifln-oride DBA = l,3-dibromo-5,5-dttnethylhydantoin DDQ = 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DET = diethyl tartrate DIAD = diisopropyl acetylene dicarboxylate DIBAL-H = diisobutylalummum hydride DIPEA = diisopropyl ethyl amine DMDO = dimethyldioxirane HMPA = hexamethylphosphortriamide EDA = lithium diisopropy-lamide Ms = methylsulfonyl MOM = methoxymethyl NBS = iV-bromosuccmimide NMO = A-methylmorpholine iV-oxide PDC = pyridinium dichromate PMP = p-methoxyphenyl THP = tetrahydropyranyl TIPS = trisiso-propylsilyl TMANO = trimethylamine A-oxide TBDMS = t-butyldimethylsilyl Tf = trifluoromethanesulfonyl TMP = 2,2,6,6-tetramethylpiperidyl TMS = trimethylsilyl Ts = p-toluenesulfonyl. 

Diisopropyl ethyl amine Trishydrofluoride Typical Procedure 92... 

Oberhaupt scheint die Reduktion in Gegenwart einer Base schneller und unter milderen Bedingungen abzulaufen. Neben N,N-Dimethyl-anilin23, das jedoch ebenfalls reduziert wird, wird Diisopropyl-ethyl-amin in Aceton empfohlen24 z.B. ... 

For esters, deprotonation is effected with triethyl amine (which favors E2), while El ionization is disfavored because it requires moving the bulky terr-butyl group into planarity. For thioesters, Ei reaction is facilitated by the thiophenyl group, while E2 reaction is slowed by use of the bulky diisopropyl ethyl amine. ... 

The ester 107 has been submitted to the Homer-Wadsworth-Emmons reaction, using diisopropyl ethyl amine as the base in the presence of lithium chloride. 

Diacetylene fatty acids were purchased from GFS. N-(2-Hydroxyethyl)-10,12-pentacosadiynamide (10) was synthesized by literatnre methods (77). 1-Amino-10,12-pentacosadiyne (11) was synthesized in fom steps from 10,12-pentacosadiynoic acid the acid in anhydrous tetrahydrofuran (THF) at 0 °C was reduced to the alcohol through treatment with hthinm alnminnm hydride (LAH, 2.5 equivalents) in diethyl ether for two hours, the alcohol was then converted to the mesylate by treatment with mesyl chloride (6 eqnivalents) in methylene chloride with diisopropyl ethyl amine over 30 minntes, the mesylate was displaced by sodium azide (1.5 equivalents) in dimethyl formamide (DMF) at 70 °C over one hour and the azide, in THF, was reduced to the amine with LAH (2 equivalents) in diethyl ether at 0 °C over one hour. N-(10,12-pentacosadiynyl)-glutamic acid (12) was prepared from 11 as follows 11 was reacted with glutaric anhydride (2 equivalents) in DMF, in the presence of diisopropylethylamine (3 equivalents), at 70 °C for 1 hour and the crade product recrystallized from a mixture of chloroform and hexanes. The identity of products were confirmed by H and C NMR. 

Under the protection of nitrogen, the substrate 2-bromo-6-methyl phenol (30.0 g, 160 mmol) and diisopropyl ethyl amine (82.9 mL, 480 mmol) were added to 0 °C dichloromethane (600 mL). Under the stirring condition, MOMCl (18.1 g, 240 mmol) was added, heated to room temperature, and reacted for 3 h. TLC showed that the reaction was completed. 1 N diluted hydrochloric acid (200 mL) was slowly added drop wise at 0 °C to adjust pH = 7. Dichloromethane (200 mL) was added to the system. The aqueous phase was extracted with dichloromethane (3 X 200 mL). The organic phases were combined, washed with saturated brine (200 mL), dried over anhydrous sodium sulfate, and hltered. The hltrate was concentrated under reduced pressure. The resulting crude product was separated and purihed by hash column chromatography (PE/EA = 100 1) to give 32 g colorless liquid Rf— 0.80, PE/EA = 10 1), 89 % yield. 

Diisopropyl ethyl amine, distilled over CaH2 and stored over 3 A molecular sieves. 

When all of the slurry is added to each reaction vessel, add distilled dry diisopropyl ethyl amine (0.5 mL, 3.12 mmol) to each well. 

The most successful imide systems for diastereoselective aldol addition reactions are, without question, the oxazolidinones 50-52 developed by Evans. These furnish syn aldol adducts with superb selectivity for a broad range of substrates (Scheme 4.5) [6, 13, 45-47). A hallmark of these system is that enolization yields exclusively the Z-enolates, which can be understood on the basis of steric considerations. Two important discoveries in the area proved critical to the unparalleled success enjoyed by Evans auxiliaries for diastereoselective aldol addition reactions. The first of these was the disclosure by Mukaiyama that the combination of di-n-butylboryl trifluorometh-anesulfonate (n-Bu2BOTf) and diisopropyl ethyl amine can be employed for the generation of dialkylboron enolates from ketones [48]. The second key observation was by Roster, who observed that aldol additions of boron enolates proceeded with higher levels of simple induction [49], This phenomenon is attributed to the short B-0 distances in the attendant Zimmer-man-Traxler transition state structure [14, 47]. 

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