4-Methylmorpholine → tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To 5 g (0.023 mol) of Boc-Valine dissolved in THF (30 mL) at −10° C. under N2 are added NMM (2.5 mL 0.023 mol) and IBCF (3 mL, 0.023 mol). The reaction mixture is stirred 15 minutes and filtered. The filtrate is added slowly to an ice-cold solution of NaBH4 (2.3 g, 0.061 mol) in H2O (10 mL) and stirred 1 hour at ice-bath temperature then 1 hour at room temperature. The reaction mixture is cooled to 0° C. and treated with saturated NaHCO3 solution, extracted with EtOAc, washed with 1M HCl saturated with NaHCO3, dried over anhydrous MgSO4, and evaporated to dryness. The crude Boc-ValCH2OH product is purified over a silica gel column eluted with 95:5 EtOAc/MeOH.

Provenance & Evidence