Sodium borohydride → HCID 18316371, compound

Participants

Reaction Steps

2-(2-Methyl-4-nitrophenylimino)-1,3-thiazolidine was prepared in a manner analogous to that described in method C2a and was alkylated with 1-bromo-3,3-dimethyl-2-butanone in a manner analogous to that described in Method D2a to give 2-(2-methyl-4-nitrophenylimino)-3-(3,3-dimethyl-2-oxobutyl)-1,3-thiazolidine. To a solution of 2-(2-methyl-4-nitrophenylimino)-3-(3,3-dimethyl-2-oxobutyl)-1,3-thiazolidine (0.022 g, 0.065 mmol) in MeOH (2 mL) was added NaBH4 (0.0096 g, 0.26 mmol) in portions. The resulting mixture was stirred at room temp for 4 h, then was separated between EtOAc (10 mL) and H2O (5 mL) and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were sequentially washed with H2O (15 mL), a saturated NaCl solution (15 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by preparative TLC (20% EtOAc/hexane) to yield 2-(2-methyl-4-nitrophenylimino)-3-(3,3-dimethyl-2-hydroxybutyl)-1,3-thiazolidine (0.024 g, 92%); FAB-MS m/z 338 ((M+H)+).

Provenance & Evidence