Borane-Dimethylamine

Add to the reaction mixture a quantity of reducing agent (e.g., sodium cyanoborohydride or borane dimethylamine (BDA)) to give a final concentration of 1.0 M. 

Add to the reaction mixture an equal volume of the reducing agent borane-dimethylamine (BDA) complex, which was previously prepared in the reaction buffer at a concentration of 125 mg/ml. 

Reduction and N-formylation of folic acid. Folic acid (2) can be converted in one step in 64% yield into folinic acid (leucovorin, 3) with borane-dimethylamine (15 equiv.) in formic acid at 40.1 Folinic acid, a metabolite of folic acid, is used... 

Diisopinocampheylborane, 117 followed by protonation Borane-Dimethylamine, 42 Borane-Tetrahydrofuran, 42 (R,R)- and (S,S)-/r ms-2,5-Dimethyl-borolanes, 119... 

Borane-Dimethylamine, 42 Dimethyl phenylsilane, 123 Diphenylsilane, 153 Lithium aluminum hydride-Sodium methoxide, 159 Potassium-Graphite, 252 Raney nickel, 265 Sodium borohydride, 278 Sodium borohydride-Molybdenum(VI) oxide, 279... 

Tin(II) chloride, 298 to other nitrogen compounds Borane-Tetrahydrofuran, 42 Tin(II) chloride, 298 of nitrogen compounds, but not nitriles and nitro compounds Acetic-formic anhydride, 1 Borane-Dimethylamine, 42 Palladium catalysts, 230 Trimethylsilyllithium-Hexamethyldisi-lane, 328... 

Triethylaluminum, 204 Triisobutylaluminum, 205 Trimethylaluminum, 22, 205 Vilsmeier reagent-Lithium tri-r-butoxy-aluminum hydride, 342 Boron Compounds Alkyldimesitylboranes, 8 Allenylboronic acid, 36 9-Borabicyclo[3.3.1]nonane, 92 Borane-Dimethylamine, 42 Borane-Dimethyl sulfide-Sodium borohydride, 25... 

Bicyclic enamines were prepared using the bicyclic ketone, tris(dimethylamino)borane, dimethylamine and potassium carbonate in an autoclave heated to 95-105 °C494. 

The Step 2 product (0.484 mmol) was treated with borane-dimethylamine complex (1.952 mmol) in 40 ml CH2C12 at 0°C followed by the dropwise addition of 254 ml boron trifluoride diethyl etherate over 30 minutes. Stirring was continued for an additional hour at ambient temperature and the mixture was then quenched with using 15 ml saturated NaHC03 solution. The solution was diluted with 60 ml CH2C12, then washed three times with 100 ml brine, dried, and concentrated. The residue was purified by flash chromatography using hexane/EtOAc, 6 1, and the product isolated in 60% yield. 

The Aloe group can be used for protection of the a-amino group instead of Boc or Fmoc as it is orthogonal to the semipermanent benzyl- or ferf-butyl-type side-chain and linker protections. This Aloe protection can be useful when some features of the peptide or pseudopeptide prevent the use of bases or acids in the deprotection step. In model studies, pseu-dometaUic hydrides (tributyltin hydride and borane-dimethylamine complex), which are neutral reagents, have been used as aUyl scavengers. 

G. N. Patwari, T. Ebata, and N. Mikami, Evidence of dihydrogen bond in gas phase phenol-borane-dimethylamine complex, J. Chem. Phys. 113, 9885-9888 (2000). 

Reductions. iyn-Selective reduction of observed with borane-pyridine in the present predominate in the reduction with LiBHEt-.-C (Ph,P)4Pd catalyzes removal of the R SC the transformation of y,8-epoxy-o(,p-un.saiurj lers by the borane-dimethylamine complex Allyl group scavengers. In the solid-nitrogen by an (V-allyloxycarbonyl group can the presence of a borane-amine complex. 

Ph P)4Pd catalyzes removal of the R SO, group from aryl perfluorosulfonates and the transformation of 7,8-epoxy-a, 3-unsaturated esters " to 8-hydroxy-a,P-unsaturated esters by the borane-dimethylamine complex. 

Deoxygenation of aromatic ketones. Borane-dimethylamine, together with TiCl4, is a mild and efficient reagent for achieving the reduction. 

Acetal cleavage Interestingly, the regioselectivity in the reductive ring opening of 4.6-O-benzylidene glucose and glucosamine derivatives by borane-dimethylamine-boron trifluoride etherate, is dependent on the solvent used. 

The extremely broad functional group tolerance of the Pd-catalysed N-depro tection of Aloe groups was a crucial design feature in a synthesis of the epoxy-quinol core of the Manumycin family of antitumour antibiotics [Scheme 8,80]. Note the convenient generation of the Pd(0) catalyst in situ from reaction of dichlorobis(triphenylphosphine)palladium(ll) with tributylstannane. The use of sodium borohydride and borane dimethylamine complex is illustrated in Schemes 8,81 and 82 respectively. 

Nickel and nickel-boron films were prepared by galvanostatic (ik = 2 A/dm2) electrodeposition at 30 °C. Compounds from higher boranes (sodium decahydroklovodecaborate, sodium dodecahydroklovododecaborate) and borane complexes (borane-pyridine, borane-morpholine, borane-dimethylamine, borane-trimethylamine) were used as a source of boron. The thickness of the films was 1-30 pm. The amount of boron in the films was determined by potentiometric... 

We also performed C02-laser heating experiments on borane-dimethylamine BH3 NH(CH3)2 to check if organic materials containing boron and nitrogen can be used for synthesis of ternary BNC compounds with diamond-like structure. Borane-dimethylamine was heated at 23 GPa to about 3000 K. Raman spectra from the heated sample area revealed the presence of cubic BN, and of liquid H2 at pressures below the solidification point of hydrogen (5.5 GPa at room temperature [71]) (Fig. 17). A Raman spectrum of the recovered white agglomerate showed a weak line of diamond in addition to the Raman bands of cubic BN. Thus, borane-dimethylamine transformed to cubic BN, diamond and hydrogen... 

Figure 17. Raman spectra of liquid and cubic BN at 0.6 GPa in a DAC after heating of borane-dimethylamine to about 3000 K at 23 GPa.

Borane, compd. with dimethylamine (1 1) Borane-dimethylamine complex. See Dimethylamine borane Borane, tributoxy-. See Tributyl borate Borates, tetra, sodium salt, anhydrous. See Sodium borate... 

---