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HRID42130

反应详情

EQUATION

反应方程式

HRID 42130 的结构方程式

REACTANTS

反应物

1
结构：CC(=O)S[C@@H]1CC[C@@]2(C)C(C1)[C@@H](O)C[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12
HCID86635597

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)S[C@@H]1CC[C@@]2(C)C(C1)C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
HCID86635596

未命名化合物

收率 77.3%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CCC[N+](CCC)(CCC)CCC.O=[Ru](=O)(=O)[O-]
催化剂HCID178419074

未命名化合物

2 次

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a stirred suspension of 3α-acetylthioandrostane-6α,17β-diol (1.40 g) in CH2Cl2 (50 mL), NMNO (1.37 g), TPAP (68 mg) and powdered molecular sieves 4 Å (2.1 g) were added at room temperature. After 2 hrs NMNO (0.7 g), TPAP (34 mg) and molecular sieves 4 Å (1 g) were added again and the reaction was stirred for further 1.5 hrs. The crude product was purified by flash chromatography (SiO2, cyclohexane:EtOAc 7:3) to give 3α-acetylthioandrostane-6,17-dione (1.07 g, 76%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.99 (1H, bb), 2.55-1.20 (23H, m), 0.86 (3H, s), 0.79 (3H, s).

WORKUP

后处理

  1. additionwere added at room temperature
  2. customThe crude product was purified by flash chromatography (SiO2, cyclohexane:EtOAc 7:3)