Ethanol → 8-Benzyl-8-azabicyclo[3.2.1]octane-3-carbonitrile

HRID 1936725Notes

Reaction equation

CC(C)([O-])C.[K+].[CH2:7]([N:14]1[CH:19]2[CH2:20][CH2:21][CH:15]1[CH2:16][C:17](=O)[CH2:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S([CH2:33][N+:34]#[C-])(C1C=CC(C)=CC=1)(=O)=O.C(O)C>C(COC)OC>[C:33]([CH:17]1[CH2:16][CH:15]2[N:14]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:19]([CH2:20][CH2:21]2)[CH2:18]1)#[N:34]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium t-butoxide (2.5 g) was added portion wise to a stirred mixture of 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (2.0 g), tosylmethyl isocyanide (2.36 g) and ethanol (2 ml) in dimethoxyethane (50 ml) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 0.5 hours and then overnight at room temperature. The mixture was then filtered and the solid residue washed with dimethoxyethane. The combined filtrates were evaporated under reduced pressure and chromatographed [SiO2; hexane:ethyl acetate (80:20)] to give 3-cyano-8-benzyl-8-azabicyclo[3.2.1]octane (0.87 g).

Workup

customovernight
customat room temperature
filtrationThe mixture was then filtered
washthe solid residue washed with dimethoxyethane
customThe combined filtrates were evaporated under reduced pressure
customchromatographed [SiO2; hexane:ethyl acetate (80:20)]

Sources & evidence

ORD record: ord-12f113a07ca046d2a6d49430a5e3ac1f
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391883B1

Reaction notes

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