Benzophenone → 2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-one

HRID 4976

Reaction equation

Cl.[N:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:9])[CH2:3]2.[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[C:18]1([C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([OH:17])[CH:3]2[C:4](=[O:9])[CH:5]3[CH2:8][N:2]2[CH2:7][CH2:6]3)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred mixture of 1-azabicyclo[2.2.1]heptan-3-one hydrochloride (1.06 g) and benzophenone (1.82 g) in dry THF (5 ml) at -78° C. under argon was added a solution of lithium bis(trimethylsilyl)amide (18 ml, 1.0M in THF). The solution was stirred at -78° C. for 1 h, allowed to warm to room temperature and stirred for 48 h. The mixture was poured onto water and extracted with dichloromethane (×4). The combined extracts were dried (Na2SO4), evaporated in vacuo, and the residue was purified by chromatography on silica using a gradient elution of 10-30% ethyl acetate in dichloromethane to afford the title compound as a white solid:

Workup

temperatureto warm to room temperature
stirringstirred for 48 h
additionThe mixture was poured onto water
extractionextracted with dichloromethane (×4)
dry with materialThe combined extracts were dried (Na2SO4)
customevaporated in vacuo
customthe residue was purified by chromatography on silica using
washa gradient elution of 10-30% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-6d347d740c6e4775b8e0120476bb6945
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05242930

Linked notes

Loading…