Benzylamine → 6-Benzyl-6-azabicyclo[3.1.0]hexan-2-one

Reaction equation

Br[C:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH:6]=1.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:8]([N:15]1[CH:2]2[CH:6]1[CH2:5][CH2:4][C:3]2=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Procedure

To a stirred solution of 2-bromocyclopent-2-enone (1.00 g, 6.21 mmol) in H2O (25 mL), tetrabutylammonium bromide (400 mg, 1.24 mmol) and benzyl amine (790 mg, 7.45 mmol) were added at room temperature. The reaction mixture was stirred for 24 hours and then extracted with EtOAc (100 mL). The organic layer was separated, washed with brine, and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue on a silica gel column with 0 to 30% EtOAc/Hexanes afforded 6-benzyl-6-azabicyclo[3.1.0]hexan-2-one. MS ESI calc'd. for C12H13NO [M+H]+ 188. found 188.