Sodium borohydride → HCID 18968908, compound

Reaction equation

[N:1]([CH:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][C:14]3[C:19]([C:7]=2[CH2:6][CH2:5]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N+]=[N-].[BH4-].[Na+]>C1COCC1.C(O)C>[NH2:1][CH:4]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][C:14]3[C:19]([C:7]=2[CH2:6][CH2:5]1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

Procedure

A solution of 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2, 1-b]azepine (1.0 g, 4.0 mmol) in dry THF (20 ml) was placed under an atmosphere of nitrogen and cooled by an ice-bath. A solution of sodium borohydride (0.17 g, 4.4 mmol) in ethanol (20 ml) was added dropwise during a period of 10 minutes and the reaction mixture was heated at reflux temperature for 20 h. The volatiles were evaporated in vacuo and the residue was purified by columm chromatography on silica gel (200 g) using dichloromethane and a mixture of ethanol and 25% NH3 (aq) (9:1) (gradient 0% to 10%) as eluent. This afforded 0.30 g of 3-amino-4-oxo-2,3,4,5-tetrahydro-1H-naphtho [2,1-b]azepine.