Sodium borohydride → 4-fluoro-N-[(1R)-3-hydroxy-1-(hydroxymethyl)propyl]benzenesulfonamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:17][C:18](OC)=[O:19])[C:13](OC)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@@H:12]([CH2:13][OH:14])[CH2:17][CH2:18][OH:19])(=[O:10])=[O:9])=[CH:6][CH:7]=1Participants
4
Procedure
To a cooled (0° C.) solution of dimethyl (2R)-2-{[(4-fluorophenyl)sulfonyl]-amino}succinate (1 equiv.) from step 1 in EtOH (10 mL/g) was added NaBH4 (5 equiv.) in 3 portions and the reaction was stirred overnight at rt. The reaction was quenched with brine (5 mL/g) and filtered. The solid was suspended in EtOAc (10 mL/g). The mother liquor was concentrated in vacuo and then saturated with NaCl. The EtOAc suspension was then filtered.