HCID 89543486, compound → HCID 89543728, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-((1-cyclopropyl-2-nitroethyl)thio)acetate (4-12, 1.46 g, 6.26 mmol) was taken up in AcOH (30 ml). To this was added zinc powder (4093 mg, 62.6 mmol) then the mixture was heated to 70° C. After stirring overnight the mixture was cooled to rt, diluted with AcOH, filtered through a pad of Celite washing with AcOH, and concentrated. The crude product was subjected to silica gel chromatography (40 g, 0-100% EtOAc/hexanes, 10 minute gradient) to afford 6-cyclopropylthiomorpholin-3-one (4-13, 355 mg, 36%) as an amber oil which solidified slowly under vacuum. 1H NMR (399 MHz, CDCl3): δ 6.65 (s, 1H); 3.65 (dt, J=13.2, 4.4 Hz, 1H); 3.54-3.46 (m, 1H); 3.32 (s, 2H); 2.47-2.39 (m, 1H); 0.98-0.89 (m, 1H); 0.67-0.58 (m, 2H); 0.41-0.25 (m, 2H).

Provenance & Evidence