反应 #1857560

反应方程式

tert-butyl ((3S,7S,8S,9S)-7-(benzyloxy)-8-butyl-9-methyl-2-oxooxonan-3-yl)carbamate

hydrogen

→

title compound

收率 85.5%

tert-butyl ((3S,7S,8R,9S)-8-butyl-7-hydroxy-9-methyl-2-oxooxonan-3-yl)carbamate

收率 85.5%

溶剂

EtOAc

反应条件

后处理

1. 1
   过滤The reaction was filtered through a pad of celite
2. 2
   洗涤the pad was washed with EtOAc
3. 3
   浓缩The filtrate was concentrated
4. 4
   其他the residue purified by flash chromatography (SiO2; EtOAc/hexanes)

实验过程

To a solution of tert-butyl ((3S,7S,8S,9S)-7-(benzyloxy)-8-butyl-9-methyl-2-oxooxonan-3-yl)carbamate (0.600 g, 1.38 mmol) in EtOAc (15 mL) was added 10% Pd/C (0.0740 g, 0.0690 mmol). The reaction flask was placed under 1 atm. of hydrogen (balloon) and stirred vigorously for 72 h. The reaction was filtered through a pad of celite and the pad was washed with EtOAc. The filtrate was concentrated and the residue purified by flash chromatography (SiO2; EtOAc/hexanes) to give the title compound as a colorless oil (0.405 g, 1.18 mmol, 85%): 1H NMR (400 MHz, CDCl3) δ 5.11 (d, J=8.3 Hz, 1H), 4.71 (dq, J=10.0, 6.4 Hz, 1H), 4.26-4.15 (m, 1H), 3.69 (ddd, J=8.7, 5.7, 2.2 Hz, 1H), 2.34-2.22 (m, 1H), 1.97 (dddd, J=15.5, 10.1, 7.7, 5.2 Hz, 1H), 1.87-1.76 (m, 1H), 1.75-1.53 (m, 5H), 1.52-1.46 (m, 1H), 1.44 (s, 9H), 1.40-1.34 (m, 1H), 1.33 (d, J=6.3 Hz, 3H), 1.30 (d, J=7.1 Hz, 1H), 1.23-1.13 (m, 2H), 1.10-1.00 (m, 1H), 0.90 (t, J=7.1 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 173.03, 154.09, 79.78, 73.54, 72.41, 52.43, 48.04, 34.24, 33.60, 28.31, 28.26, 27.61, 23.41, 19.21, 17.61, 13.97; ESIMS m/z 407 ([M+Na+CH3CN]+).

来源