Dimethyl Sulfoxide → HCID 18723527, compound

Participants

Reaction Steps

To a solution of 0.1 mL (1.2 mmol) of oxalyl chloride in 10 mL of CH2Cl2 at −78° C. was added 0.17 mL (2.37 mmol) of DMSO and the reaction mixture was stirred for 10 min. To this reaction mixture at −78° C. was added a solution of 0.26 g (0.59 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-hydroxymethylpyrrolidine in 10 mL of CH2Cl2. After stirring for 10 min. at −78° C., 0.41 mL (2.9 mmol) of Et3N was added and the reaction was allowed to warm to rt. The reaction mixture was poured into ether and washed twice with sat'd NaHCO3 solution and once with sat'd NaCl solution. The organic fraction was dried over NaSO4, filtered and the filtrate was concentrated to give 0.29 g of the title compound. 1H NMR (CDCl3) δ9.85, 9.70 (d, 1H, J=2.0 Hz),7.86-7.91 (m, 2H), 7.48-7.55 (m, 3H), 7.10-7.18 (m, 2H), 6.94-7.00 (m, 2H); Mass Spectrum (ESI) m/e=445 (M+1).

Provenance & Evidence