反应 #2200584

反应方程式

(S)-N-[(1S,2R,3S)-1-cyano-2-methyl-3-tetrahydropyranyloxybutyl]-p-toluenesulfinamide

(S)—N-[(1S,2R,3S)-1-cyano-2-methyl-3-tetrahydropyranyloxybutyl]-p-toluenesulfinamide

HCl

→

(3S,4R,5S)-3-amino-4-methyl-5-methyl-2-oxotetrahydrofuran hydrochloride

收率 100.0%

反应条件

后处理

1. 1
   洗涤The reaction mixture was washed with dichloromethane, and it
2. 2
   其他was evaporated in order

实验过程

A solution of (S)-N-[(1S,2R,3S)-1-cyano-2-methyl-3-tetrahydropyranyloxybutyl]-p-toluenesulfinamide (8) (200 mg, 0.57 mmol) in 6N HCl (14 ml) was refluxed for 6 hours. The reaction mixture was washed with dichloromethane, and it was evaporated in order to obtain (3S,4R,5S)-3-amino-4-methyl-5-methyl-2-oxotetrahydrofuran hydrochloride (9) (94 mg, 100%). [α]D=−18° (c 1.4; MeOH); IR (nujol) 3526, 2924, 2854, 1771, 1581, 1504, 1462, 1385, 1355, 1315, 1260, 1209 cm−1; 1H NMR (250 MHz, D2O) δ 4.61 to 4.54 (m, 2H); 2.72 (broad quintuplet, J=7.5 Hz, 1H); 1.40 (d, J=6.6 Hz, 3H); 1.11 (d, J=7.3 Hz, 3H); 13C NMR (50 MHz, D2O) δ 174.3; 85.2; 52.3; 38.1; 19.5; 13.0; MS (CI) m/z 130 [M+H]+. HRMS: calculated for C6H12NO2 (M+H), 130.08680; found, 130.08604.

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