反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
PROCEDURE
实验过程
Following the general procedure, 5,6,7,8-tetrahydroquinoxalin-5-ylamine (263 mg, 1.76 mmol), CALB (45 mg) and EtOAc (7.0 mL) were stirred for 2 hours. The conversion determined from 1H NMR by integration of the peaks at 4.94 ppm (CHNHAc) and 4.01 ppm (CHNH2) was 50%. Flash chromatography of the material on silica gel using 1:4 MeOH:EtOAc followed by 1:1:4 NH4OH:MeOH:EtOAc furnished the (R)-N-(5,6,7,8-tetrahydroquinoxalin-5-yl)acetamide ((157 mg, 47%) in 98% ee (chiral GC method: 130° C. for 180 min, (S)-enantiomerrt=183.5 min, (R)-enantiomerrt=183.7 min); [α]D=−78° (c 1.40, CHCl3); 1H NMR (CDCl3, 300 MHz) δ 1.62-1.75 (m, 1H), 1.85-2.04 (m, 2H), 2.06 (s, 3H), 2.48-2.57 (m, 1H), 2.90-3.13 (m, 2H), 4.96-5.03 (m, 1H), 6.34 (br s, 1H), 8.35 (d, 1H, J=2.4 Hz), 8.39 (d, 1H, J=2.4 Hz); 13C NMR (CDCl3) δ 19.9, 23.6, 29.7, 31.8, 50.6, 142.1, 143.3, 152.0, 154.0, 170.7; MS m/z: 214 (M+Na+). The unreacted (S)-5,6,7,8-tetrahydroquinoxalin-5-ylamine (was isolated in 45% yield (118 mg) and 99% ee ((S)-enantiomern=25.9 min, (R)-enantiomerrt=29.0 min); [α]D=+61° (c 0.71, CHCl3); 1H NMR (CDCl3, 300 MHz): δ 1.62-1.79 (m, 1H), 1.80-2.18 (m, 4H), 2.18-2.30 (m, 1H), 2.91-3.01 (m, 2H), 4.07 (dd, 1H, J=8.4, 5.4 Hz), 8.32-8.38 (m, 2H); 13C NMR (CDCl3): δ 19.7, 31.7, 32.2, 51.5, 142.0, 142.5, 152.6, 155.4; MS m/z: 150 (M+H+), 133 (M−NH2).