Dimethyl Sulfoxide → HCID 88117181, compound

Participants

Reaction Steps

A solution of oxalyl chloride (0.6 mL, 7 mmol) in 35 mL CH2Cl2 was cooled to −78° C. and DMSO (1 mL, 14.1 mmol) was added dropwise. After stirring for 20 min a solution of Benzyl 1-{[(3R,4S)-3-(3-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-1-yl]methyl}cyclohexane carboxylate (2.5 g, 5.88 mmol, from Step C) in 35 mL CH2Cl2 was added. The mixture was stirred for 20 min more then triethylamine (4 mL, 29.5 mmol) was added. The cooling bath was removed and the mixture was stirred for 4h. 100 mL CH2Cl2 was added and the mixture was washed with 1 M NaOH then water and sat'd sodium chloride. The organic layer was dried over magnesium sulfate and concentrated. Flash chromatography (90 g silica, 5/1 hexane/EtOAc) gave the desired aldehyde. 1H NMR (500 MHz, CDCl3) δ1.25-1.43 (m, 6H), 1.58-1.63 (m, 4H), 2.15-2.19 (m, 2H), 2.62-2.73 (m, 2H), 2.83-2.87 (m, 1H), 2.92-3.01 (m, 2H), 3.44-3.51 (m, 1H), 5.11-5.21 (dd, 2H), 6.9-6.97 (m, 1H), 6.98-7.13 (m, 2H), 7.23-7.4 (m, 6H), 9.6 (s, 1H).

Provenance & Evidence