N-Fluorobenzenesulfonimide → HCID 71254298、化合物
反応式
[O:1]=[C:2]1[CH:7]([C:8]([O:10][C@H:11]2[CH2:16][C@@H:15]([CH3:17])[CH2:14][CH2:13][C@@H:12]2[CH:18]([CH3:20])[CH3:19])=[O:9])[CH2:6][CH2:5][CH2:4][NH:3]1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:31])(=O)=O)=CC=1>C(O)C>[F:31][C@@:7]1([C:8]([O:10][C@H:11]2[CH2:16][C@@H:15]([CH3:17])[CH2:14][CH2:13][C@@H:12]2[CH:18]([CH3:20])[CH3:19])=[O:9])[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:1]参加物
4
反応条件
- 温度
- 0 °C
実験手順
(1S,2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexyl 2-oxo-3-piperidinecarboxylate (1 wt) is dissolved in ethanol (1.5 vol) and N-fluorobenzenesulfonimide (NFSI) (1.07 wt) added, followed by [(S)-BINAP]Pd(CH3CN)2(OTf)2 (0.038 wt) at 20° C. Residual NFSI and catalyst were washed in with ethanol (3 vol). The jacket is cooled to 0° C. and 2,6-lutidine (0.21 vol) charged slowly, maintaining the temperature below 20° C. The jacket temperature is then raised to 20° C. The reaction mixture is stirred for 24 h, cooled to 0° C. and stirred for an additional 2 h. The solids are isolated by filtration, washing with ethanol (3 vol) and dried under vacuum at 40° C. The dried crude solid is charged to a reactor, and dichloromethane (5 vol) added. The dichloromethane phase is washed sequentially with 2M aqueous NaOH (3 vol), water (3 vol), 5% w/w aqueous HCl (3 vol) and water (3 vol). The dichloromethane extract is transferred to a rotary evaporator and solvent swapped with n-heptane under reduced pressure to give a mobile slurry and a final volume of ca 11 vol. The product is isolated by filtration, washed with heptane (3 vol) and dried under vacuum at 40° C.