1,2-Dichloroethane → ((3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl)(4-(1-cyclohexyl-2-(diethylamino)ethyl)piperazin-1-yl)methanone

Participants

Reaction Steps

To a solution of (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine 3-carboxylic acid A-2 (40 mg, 0.138 mmol) in dichloromethane (10 mL) was added 4-methylmorpholine (0.023 mL, 0.208 mmol), HOBt (20.6 mg, 0.152 mmol), EDC (39.8 mg, 0.208 mmol), and piperazine K-2 (41.9 mg, 0.138 mmol). The reaction mixture was stirred at room temperature for 18 hrs. The reaction mixture was concentrated, purified by preparative TLC (10:1, CHCl3: 2N NH3 in MeOH) to give a yellow oil, to which was added HCl (1M in ether) and the resulting mixture was concentrated to give the title compound. ESI-MS calc. for C31H50F2N40: 532. Found: 533 (M+H). H1 NMR (500 MHz, CD3OD) δ 7.54–7.40 (m, 1H), 7.00–6.82 (m, 2H), 3.92–3.82 (m, 1H), 3.70–3.40 (m, 3H), 3.40–3.25 (m, 2H), 3.24–3.18 (m, 2H), 3.00–2.80 (m, 2H), 2.78–2.42 (m, 8H), 2.40–2.10 (m, 4H), 1.82–1.60 (m, 6H), 1.41–1.00 (m, 19H),

Provenance & Evidence