4-Methylmorpholine → HCID 22458227, compound

Participants

Reaction Steps

A mixture of 500 mg (1.5 mmol) of 4-(3-(4-fluorophenyl)-3-(RS)-hydroxypropyl)-1-(t-butoxycarbonyl) piperidine (from EXAMPLE 188, Step B), 351 mg (3.0 mmol) of 4-(methyl)morpholine and 800 mg of 4 A molecular sieves in 10 _mL of CH2Cl2 at 0° C. was treated with 35 mg (0.1 mmol) of tetrapropylammonium perruthenate. The cooling bath was removed and the mixture was stirred at rt for 1 h. The mixture was filtered and the filtrate was concentrated. Flash chromatography on 15 g of silica gel using 3:1 v/v hexanes/ether afforded 386 mg (78%) of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.10-1.19 (m, 2H), 1.43-1.49 (m, 1H), 1.45 (s, 9H), 1.58-1.70 (4H), 2.65-2.70 (m, 2H), 2.70 (t, J=7.5, 2H), 4.054.1 1 (m, 2H), 7.11-7.15 (m, 21), 7.97-8.00 (m, 2H).

Provenance & Evidence