Formaldehyde → HCID 86610913, compound

Participants

Reaction Conditions

Reaction Steps

In a pressure tube, 50 mg (0.0997 mmol) 3-[(3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-(4-fluorophenyl)pyrrolidin-1-yl]cyclopent-2-en-1-one (Example 3, step F), 10.5 mg (0.3489 mmol) paraformaldehyde, and 20.3 mg (0.2493 mmol) dimethylamine hydrochloride was dissolved in ethanol (4 mL). The tube was sealed and heated in an oil bath for 3 hr at 90° C. The reaction mixture was cooled to RT, the tube was opened and the solvent removed under vacuum. The residue was partitioned between of 5 mL 1N aq. NaOH and EtOAc (3×5 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and the solvent removed under vacuum to provide a yellow oil. The resulting oil was purified by prep TLC on silica gel eluting with methylene chloride/methanol (9/1). The more polar UV active band was isolated to afford the title compound as a glassy yellow solid. 1H-NMR (CD3OD) rotamers: δ: 1.44 (d, 3H, 6.5 Hz), 2.4-2.90 (m, 10H), 3.4-4.6 (m, 8H), 4.82 (br. s, 1H), 6.97 (t, 2H, 8.5 Hz), 7.23 (br. s, 2H), 7.69 (s, 2H), 7.80 (s, 1H)ppm. MS: 559.1 (MH+) observed.

Provenance & Evidence