1,2-Dichloroethane → HCID 58780684, compound

Participants

Reaction Steps

To a solution of (3S,4R)-1-tert-butyl-3-(2,4-difluorophenyl)-piperidine-4-carboxylic acid A-4 (30 mg, 0.101 mmol) in dichloromethane (5 mL) was added 4-methylmorpholine (0.017 ml, 0.151 mmol), HOBt (15 mg, 0.111 mmol), EDC (29 mg, 0.1514 mmol), and piperazine K-2 (30.6 mg, 0.101 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then concentrated, purified by preparative TLC (10:1, CHCl3:2N NH3 in MeOH) to give a yellow oil, to which was added HCl (1.0 M in ether) and the resulting mixture was concentrated to give the title compound as a mixture of two diastereomers, D1 and D2. ESI-MS calc. for C32H52F2N4O: 546. Found: 547 (M+H). D1: NMR (500 MHz, CD3OD) 7.40–7.27 (m, 1H), 6.94–6.82 (m, 2H), 3.68–3.40 (m, 5H), 3.395–3.00 (m, 5H), 2.80–2.20 (m, 11H), 1.94–1.60 (m, 6H), 1.50–0.84 (m, 20H). D2: NMR (500 MHz, CD3OD) 7.40–7.27 (m, 1H), 6.94–6.82 (m, 2H), 3.68–3.00 (m, 10H), 2.80–2.2 (m, 11H), 2.00–1.60 (m, 6H), 1.40–0.80 (m, 20H).

Provenance & Evidence