Sodium borohydride → (5)-Tert-butyl 3-(3-(hydroxymethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 3-(3-formylphenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (2.71 g, 6.58 mmole) was dissolved in methanol (66 ml). The solution was cooled to 0° C. in an ice bath. NaBH4 was added to the cooled solution and the resulting reaction mixture was stirred for 30 min. The reaction was confirmed to be complete by tlc and HPLC/MS. The reaction was concentrated under reduced pressure and then partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×). The combined organics were washed with H2O (2×) and brine (2×). The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by flash column using EtOAc/hexanes. Yield=1.3 g. MS (m/z) 415 [M+14]+.

Provenance & Evidence