Sodium borohydride → HCID 66704434, compound

Participants

Reaction Steps

To a solution of ethyl 2-(3-(tert-butoxycarbonyl(methyl)amino)-1-(5-chloro-2-methylphenyl) propoxy)acetate (800 mg, 2 mmol) in MeOH (16 mL) was added NaBH4 (305 mg, 8 mmol) in portions while the temperature was lower than 40° C. After addition, the mixture was stirred at room temperature for 2-3 h. The solvent was removed in vacuo to the residue, which was partitioned between water and ethyl acetate. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on silica gel chromatography to afford tert-butyl 3-(5-chloro-2-methylphenyl)-3-(2-hydroxyethoxy)propyl(methyl)carbamate (400 mg, 56%). 1H NMR (CDCl3, 400 MHz) δ 1.22 (m, 3H), 1.43 (m, 9H), 1.87 (m, 2H), 2.21 (s, 3H), 2.87 (s, 3H), 3.39 (m, 2H), 3.80 (m, 1H), 4.00 (m, 1H), 4.61 (m, 1H), 7.08 (m, 2H), 7.37 (m, 1H).

Provenance & Evidence