Dimethyl Sulfoxide → HCID 59924629, compound

Participants

Reaction Steps

A solution of oxalyl chloride (1.03 mL, 11.8 mmol) in 60 mL CH2Cl2 was cooled in a dry ice/acetone bath. DMSO (1.67 mL, 23.6 mmol) was added dropwise. The mixture was stirred for 15 min then a solution of benzyl (2R)-cyclohexyl[(3S,4R)-3-(3-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-1-yl]ethanoate (4.2 g, 9.8 mmol, from Step C) in 70 mL CH2Cl2 was added dropwise. After stirring for 15 min TEA (6.8 mL, 49 mmol) was added in 10 mL CH2Cl2. The mixture was warmed to rt and stirred for 2 h. The solution was poured into a speparatory funnel and diluted with 200 mL CH2Cl2 and washed with 1 N NaOH (2×), water and sat'd NaCl. The organic portion was dried over sodium sulfate and concentrated. Flash chromatography (150 g silica, 0→30% EtOAc/hexanes) gave the desired aldehyde. 1H NMR (500 MHz, CDCl3) δ0.95-1.05 (m, 2H), 1.14-1.29 (m, 3H), 1.6 (br d, 1H), 1.66-1.83 (m, 4H), 1.93 (br d, 1H), 2.65-2.69 (m, 1H), 2.88-2.93 m, 1H), 3.15 (dd, 1H), 3.20-3.24 (m, 2H), 3.27-3.30 (m, 1H), 3.55 (dd, 1H), 5.18 (d, 1H), 5.19 (d, 1H), 6.89-6.97 m, 3H), 7.23-7.27 (m, 1H), 7.33-7.4 (m, 5H).

Provenance & Evidence