4-Toluenesulfonyl chloride → Androsterone tosylate

HRID 64250

反応式

HRID 64250 の反応式
[CH3:1][C@@:2]12[C@H:11]3[CH2:12][CH2:13][C@:14]4([CH3:20])[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]4[C@@H:10]3[CH2:9][CH2:8][C@H:7]1[CH2:6][C@@H:5]([OH:21])[CH2:4][CH2:3]2.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[S:28]([O:21][C@H:5]1[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:11]2[CH2:12][CH2:13][C@@:14]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:19])[CH2:6]1)([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29]

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 441302Epiandrosterone

生成物 1

HCID 14056196Androsterone tosylate収率 87%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

In a 25 mL round bottom flask, trans-androsterone (1.00 g, 3.44 mmol) and p-toluenesulfonyl chloride (1.51 g, 7.91 mmol) was dissolved in in pyridine (4.30 mL). The reaction mixture was stirred continuously at room temperature. After 24 h, the reaction mixture was quenched by adding H2O (10 mL) and it was extracted with CH2Cl2 (3×20 mL). All organic layers were collected, combined together and washed over HCl (3×20 mL, 2 M), brine solution (3×20 mL), and H2O (3×20 mL), dried over Na2SO4, and concentrated under reduced pressure afforded 3β-tosyloxy-5α-androstan-17-one (1.33 g, 87%) as a white solid. 1H NMR (300 MHz, CDCl3): d 7.79 (dt, J=8.3, 1.9 Hz, 2H), 7.33 (dd, J=8.0, 0.5 Hz, 2H), 4.42 (h, J=5.9 Hz, 1H), 2.44 (s, 3H), 2.38-2.47 (m, 1H), 1.99-2.11 (m, 1H), 1.86-1.95 (m, 1H), 1.78-1.80 (m, 1H), 1.71-1.77 (m, 2H), 1.65-1.69 (m, 1H), 1.56-1.64 (m, 3H), 1.44-1.55 (m, 3H), 1.30-1.31 (m, 1H), 1.28-1.29 (m, 2H), 1.22-1.24 (m, 1H), 1.18-1.20 (m, 1H), 1.04-1.16 (m, 1H), 0.85-1.00 (m, 2H), 0.84 (s, 3H), 0.80 (s, 1H), 0.60-0.69 (m, 1H).

後処理

  1. customthe reaction mixture was quenched
  2. additionby adding H2O (10 mL) and it
  3. extractionwas extracted with CH2Cl2 (3×20 mL)
  4. customAll organic layers were collected
  5. washwashed over HCl (3×20 mL, 2 M), brine solution (3×20 mL), and H2O (3×20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fbc8cebf58274364a5624d0cf85f7fa3
出典データセット
uspto-grants-2016_09
特許番号
US09447139B2

関連ノート

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