Sodium Sulfite → HCID 57659757, compound

Participants

Reaction Steps

(5S)-tert-Butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-cyclopropyl-3-hydroxypyrrolidine-1-carboxylate (33) (2.72 g, 7.32 mmol) was dissolved in CH2Cl2 (35 mL). NaHCO3 (2.76 g, 32.9 mmol) and Dess-Martin periodinane (4.65 g, 10.98 mmol) were added and the resulting suspension was stirred at rt for 2 h. A mixture of sat. aq. NaHCO3 and sat. aq. sodium sulfite (20 mL, 1/1) was added and the resulting solution was stirred for 15 minutes. The biphasic mixture was extracted with CH2Cl2 (30 mL) and the organic phase was dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1 to give 1.54 g (56%, 3 steps) of (5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-cyclopropyl-3-oxopyrrolidine-1-carboxylate (34). Retention time (min)=2.628, method [2], MS (m/z) 392.2 (M+Na)+.

Provenance & Evidence