Sodium borohydride → HCID 70642497, compound

Participants

Reaction Steps

To a mixture of (2S,4S)-ethyl 2-(tert-butoxycarbonylamino)-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methylhexanoate (7.2 g, 15.2 mmol) in EtOH (100 mL) was added NaBH4 (5.0 g, 131 mmol) in portions such that the temperature remained lower than 40° C. The mixture was stirred at rt for 12 h. TLC showed the starting material had been consumed. The solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, and evaporated to produce tert-butyl (2S,4S)-1-hydroxy-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methylhexan-2-ylcarbamate (5.8 g, 88%). MS: 434 (M++1)

Provenance & Evidence