Sodium borohydride → Benzyl 3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate
Reaction equation
[CH:1]([CH:3]1[CH2:9][CH:8]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1)=[O:2].[BH4-].[Na+]>O1CCCC1>[OH:2][CH2:1][CH:3]1[CH2:4][CH:5]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH:8]([CH2:7][CH2:6]2)[CH2:9]1Participants
4
Procedure
To a solution of EXAMPLE 84B (3.4 g) in tetrahydrofuran (40 mL) was added NaBH4 (0.5 g). The mixture was stirred overnight. The solvent was evaporated and the residue was added to ethyl acetate (300 mL) and water (50 mL). The organic layer was washed with water and brine, dried over Na2SO4, and filtered. Evaporation of the solvent gave the crude title compound.