Benzyl chloroformate → 5-benzyloxycarbonylaminospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one
Reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3.[C:14](Cl)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>N1C=CC=CC=1>[CH2:17]([O:16][C:14]([NH:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-aminospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (1.35 g.) in pyridine (13.5 ml.) was added carbobenzyloxy chloride (30% toluene solution, 7 g.) under ice-cooling, and the mixture stirred for one hour. The reaction mixture was poured into ice-hydrochloric acid (14 ml.) and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to remove the solvent. The residue was recrystallized from ethanol. By the above procedure there was obtained 5-benzyloxycarbonylaminospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one as pale yellow needles, m.p. 118°-119° C. Yield 1.57 g.