反応 #92528

反応方程式

trans-androsterone

p-toluenesulfonyl chloride

→

3β-tosyloxy-5α-androstan-17-one

収率 87.0%

溶媒

pyridine

反応条件

後処理

1. 1
   その他the reaction mixture was quenched
2. 2
   workup.ADDITIONby adding H2O (10 mL) and it
3. 3
   抽出was extracted with CH2Cl2 (3×20 mL)
4. 4
   その他All organic layers were collected
5. 5
   洗浄washed over HCl (3×20 mL, 2 M), brine solution (3×20 mL), and H2O (3×20 mL)
6. 6
   乾燥dried over Na2SO4
7. 7
   濃縮concentrated under reduced pressure

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).

出典