Ethylene Glycol → HCID 53820814, compound

Participants

Reaction Steps

A solution of 71 mg (0.19 mmol) of 4-(3-(4-fluorophenyl)-3-oxo-propyl)-1-(benzyloxycarbonyl) piperidine (from EXAMPLE 189, Step B), 0.05 mL (0.9 mmol) of ethylene glycol and 5 mg (0.26 mmol) of p-toluene sulfonic acid x H2O in 3 mL of toluene was heated at 80° C. After 1 h, and additional 5 mg of p-toluene sulfonic acid×H2O was added and the resulting mixture was heated at reflux. After 2 h, the mixture was cooled and partitioned between 30 mL of ether and 10 mL of 1.0 N NaOH. The organic layer was separated, dried and concentrated. Flash chromatography on 4 g of silica gel using 3:1 v/v hexanes/ether afforded 66 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.00-1.10 (m, 2H), 1.261.36 (3H), 1.50-1.60 (m, 2H), 1.86-1.89 (m, 2H), 2.65-2.75 (m, 2H), 3.71-3.78 (m, 2H), 3.96-4.03 (m, 2H), 4.064.16 (m, 2H), 5.10 (s, 2H), 6.99-7.04 (m, 2H), 7.26-7.40 (7H).

Provenance & Evidence