6,6-dimethyl-3-azabicyclo hexane

Bromonitromethane is used for the preparation of nitrocyclopropane. The reaction of /V-be 11 zylmaleimide and bromonitromethane in the presence of base gives the azabicyclo[3.1.0] hexane ring system. Many bases have been tried to improve the yield however, amidine base, particularly 1,2-dimethyl-l, 4, 5, 6-tetrahydropyrimidine (DMTHP), gives the best yield... 

Domino-Heck Reactions-General Procedure 5.6 mg (25 pmol) of palladium(II) acetate and 55 pmol of the arsine ligand were dissolved in 3 ml of dry dimethyl formamide and the solution was stirred at 65°C (40°C for trimethylsilylacetylene) for 15 mitt Then, 127 mg (1.35 mmol) N-Benzoyl-2-azabicyclo[2.2.1]hept-5-en-3-one, 1 mmol of the aryl compound. Four hundred and eighty-eight microliters (3.50 mmol) of triethylamine, and 3.00 mmol of the phenylacetylene (or silylmethyl-acetylene) were added rapidly in one portion. The mixture was heated at the same temperature for 24 h. After cooling down to room temperature 50 ml of brine were added, the reaction mixture was extracted with ethyl acetate and dried over MgSO. The solvent was evaporated, the residue purified by column chromatography (n-Hexan-Ethyl acetate 4 1). 

N-Benzylmaleimide (500 g, 2.67 mole), 90% bromonitromethane (831 g, 5.34 mole), powdered molecular sieves 200 mesh (2020 g) and toluene (12 dm3) were stirred under nitrogen at -10°C. 1,2-Dimethyl-l,4,5,6-tetrahydropyrimidine (616 g, 5.49 mole) was added slowly over about 3 h maintaining the reaction temperature at <-8°C throughout the addition. After completion of the addition, the reaction mixture was stirred for 1.5 h at 25°C, filtered under a nitrogen atmosphere in a sealed pressure filter to remove sieves and resulting tar, and the sieves were washed with toluene (2 L). The combined filtrates were washed with 2 N dilute hydrochloric acid (3 times 750 cm3), treated with carbon (50 g) at 70°C, 1 h filtered, concentrated, and triturated with 2-propanol (about 4 dm3) to obtain crystals of the (la,5a,6a)-3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane (223 g, 34%) melting point 116°-118°C. 

Chemical Name V-(3,5-dichlorophenyl)-l,2-dimethylcyclopropane-l,2-dicarboximide 3-(3,5-dichlorophenyl)-l,5-dimethyl-3-azabicyclo[3,l,0]hexane-2,4-dione CAS Registry No 32809-16-8... 

Recently, Laurent prepared 6-methyl- and 6,6-dimethyl-5-phenyl-l-azabicyclo[3.1.0]hexane (27) by hydroboration of the 3-allylaziridines 25 to the alcohols 26, followed by bromination and cyclization. 

M., Tong, W, and Vater, E.J. (2004) Process and intermediates for the preparation of (lR,2S,5S)-6,6-dimethyl-3-azabicyclo[3,l,0]hexane-2-carboxylates or salts thereof via asymmetric esterification of caronic anhydride. Patent 2004-US19135, 2004113295, 20040615,... 

Berranger, T. and Demonchaux, P. (2008) Process for preparation of optically pure 6,6-dimethyl-3-azabicyclo[3.1.0]hexane derivatives. 2007-US25809, 2008082508, 20071218, filed Dec. 18, 2007 and issued July 10, 2008. 

Kwok, D.-L., Lee, H.-C., and Zavialov, LA. (2009) Dehydrohalogenation process for preparation of intermediates useful in providing 6,6-dimethyl-3-azabicyclo[3.1.0]hexane compounds. Patent 2008-US84174, 2009073380, 20081120, filed Nov. 20, 2008 and issued June 11, 2009. 

The formation of azabicyclohexenes 178 and 179 from the irradiation of azirine 177 clearly proceeds via a nitrile ylide intermediate since the formation of these compounds is entirely suppressed when the irradiation is carried out in the presence of an added dipolarophile. For example, when dimethyl acetylenedicarboxylate is used, cycloadduct 183 was the only product isolated. The fact that the photolysis of 177 produces a nitrile ylide intermediate which could be trapped by an added dipolarophile (i.e., as 183) eliminates a [2-f2]cycloaddition of the azirine C=N double bond with the olefin and subsequent rearrangement of a hypothetical azatricyclo[2.1.1.0 ]hexane intermediate (184) as the mechanism for the formation of the azabicyclo[3.1.0]hex-2-ene system. 

Dichlorophenyl)-l,5-dimethyl-3-azabicyclo [3.1.0] hexane-2,4-dione [32809-16-8] Ci3HnCl2N02 MW = 284.14... 

Boceprevir oxidation of 6,6-dimethyl-3-azabicyclo[3.1.0] hexane by monoamine oxidase. 

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