Sodium borohydride → HCID 21064711, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:6][CH:5]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[N:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-(2-tert-Butoxycarbonylamino-acetyl)-nicotinic acid methyl ester (132.7 mg, 0.451 mmol) was dissolved into 3 mL of MeOH. To this was added sodium borohydride (18.96 mg, 0.50 mmol) in one portion. After 0.5 h, the reaction mixture was concentrated on a rotary evaporator. The residue was dissolved into 20 mL of EtOAc. The organic phase was washed with 2×20 mL NH4Cl and 1×20 mL of brine, dried (MgSO4) filtered and concentrated to give 133 mg, 99.5% of 6-(2-tert-butoxycarbonylamino-1-hydroxy-ethyl)-nicotinic acid methyl ester.