Isopregnanolone → 5alpha-Pregn-2-en-20-one

HRID 244244

反応式

HRID 244244 の反応式
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:23])[CH2:9][CH2:10][C@@H:11]3[C@@:16]4([CH3:22])[CH2:17][CH2:18][C@H:19](O)[CH2:20][C@@H:15]4[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].C(N(S(F)(F)F)CC)C>ClCCl>[CH3:1][C:2](=[O:3])[C@@H:4]1[C@:8]2([CH3:23])[C@H:7]([C@H:12]3[C@H:11]([CH2:10][CH2:9]2)[C@:16]2([CH3:22])[C@H:15]([CH2:20][CH:19]=[CH:18][CH2:17]2)[CH2:14][CH2:13]3)[CH2:6][CH2:5]1

参加物

4

反応物 2

HCID 92787IsopregnanoloneHCID 123472(Diethylamino)sulfur trifluoride

生成物 1

HCID 2468835alpha-Pregn-2-en-20-one収率 25%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 5α-pregnan-3β-ol-20-one (3.75 g, 11.8 mmol) in anhydrous dichloromethane (200 mL) at −78° C. under argon atmosphere was added diethylaminosulfur trifluoride (DAST) (2.30 mL, 17.7 mmol) and the resulting solution stirred over a period of 1 h at −78° C. The solution was then directly evaporated with silica gel and purified by FCC with EtOAc/hexanes (2:98) as eluant to give the desired compound 11 (880 mg, 25%) with a ratio of C2-C3 alkene vs. C3-C4 alkene isomer of 96:4. 1H NMR (acetone-d6) δ: 0.60 (s, 18-CH3), 0.78 (s, 19-CH3), 0.75-2.40 (residual CH and CH2), 2.07 (s, 21-CH3), 2.60 (t, J=9.1 Hz, 17α-CH), 5.57 (m, 2-CH and 3-CH). 13C NMR (CDCl3) δ: 11.7, 13.4, 20.9, 22.7, 24.4, 28.6, 30.2, 31.6, 31.7, 34.6, 35.6, 39.1, 39.7, 41.4, 44.2, 53.9, 56.7, 63.9, 125.8, 125.9, 209.8. LRMS for C21H32O [M+H]+: 301.1 m/z.

後処理

  1. customThe solution was then directly evaporated with silica gel
  2. custompurified by FCC with EtOAc/hexanes (2:98) as eluant

出典と根拠

ORDレコード
ord-d6a18d643eca42d4ba0ca71229668b2d
出典データセット
uspto-grants-2014_02
特許番号
US08653054B2

関連ノート

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