4-Toluenesulfonyl chloride → Androsterone tosylate

HRID 64250

Reaktionsgleichung

Reaktionsgleichung von HRID 64250
[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]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 441302Epiandrosterone

Produkt 1

HCID 14056196Androsterone tosylateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fbc8cebf58274364a5624d0cf85f7fa3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447139B2

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