Acetic Acid → HCID 11841701, compound

Reaction equation

[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>C(O)C>[C:1]([NH:4][C@@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@H:6]1[OH:15])(=[O:3])[CH3:2]

Participants

Procedure

To a solution of the 2-acetamido-3,4-dihydronaphthalen-1(2H)-one from Step A in absolute ethanol (150 ml) was added sodium borohydride (2.0 gms, 0.05 m) in portions. The reaction mixture was stirred at room temperature for 1/2 hour. Acetic acid was added dropwise to destroy the excess sodium borohydride. The reaction mixture was poured into water and extracted with ethyl acetate (3×150 ml). The ethyl acetate was washed with saturated aqueous sodium chloride (150 ml) and dried over anhydrous sodium sulfate. After filtration the solvent was removed under reduced pressure to yield 5.5 gms (54%, over Steps A and B), of product as a solid.