Dimethyl Sulfide → Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-8-hydroxydecanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-8-oxodecanoic acid in anhydrous THF at 0° C. under a nitrogen atmosphere was added slowly a solution of BH3.Me2S in THF (2 M, 2 eq.). The mixture was stirred for 5 min at 0° C. and 3 hr at 55° C. The reaction was quenched with MeOH and partitioned between EtOAc and sat. aq. NaHCO3. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The obtained product was used in the next step without purification. MS (ES) C16H31NO5 requires: 317, found: 318 (M+H)+.

Provenance & Evidence