Hydrochloric Acid → HCID 22458230, compound

Participants

Reaction Steps

A mixture of 1.29 g (5.0 mmol) of 3-(1-(t-butoxycarbonyl)piperidin-4-yl)propionamide (from EXAMPLE 98, Step B) and 1.65 mL (15.0 mmol) of 4-methylmorpholine in 25 mL of CH2Cl2 at 0° C. was treated with 0.70 mL of isobutyl chloroformate. The resulting mixture was stirred cold for 15 min, then treated with 0.78 g (8.0 mmol) of O,N-dimethylhydroxylamine×HCl. The resulting mixture was stirred cold for 3.5 h, quenched with 100 mL of 0.5 N KHSO4, then extracted with 200 mL of ether. The extract was washed with 100 mL of 1.0 N NaOH, 50 mL of sat'd NaCM, dried and concentrated. Flash chromatography on 60 g of silica gel using 10:1 v/v, then 3:1 v/v CH2Cl2/EtOAc as the eluant afforded 1.31 g (91%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 1.07-1.18 (m, 2H), 1.38-1.69 (5H), 1.45 (s, 9H), 2.45 (t, J=7.6, 2H), 2.68 (app t, J=12.4, 2H), 3.18 (s, 3H), 3.69 (s, 3H), 4.05-4.11 (m, 2H).

Provenance & Evidence