Water → (3beta, 5alpha)-Androst-16-en-3-ol 4-methylbenzenesulphonate

HRID 329356

Reaction equation

HRID 329356 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C@:13]12[CH2:30][CH2:29][C@H:28]3[C@@H:18]([CH2:19][CH2:20][C@@H:21]4[C@:26]3([CH3:27])[CH2:25][CH2:24][C@H:23]([OH:31])[CH2:22]4)[C@@H:17]1[CH2:16][CH:15]=[CH:14]2.C[C@]12CC[C@H]3[C@@H](CC[C@@H]4[C@]3(C)CC[C@H]([OH:51])C4)[C@@H]1CCC2=O.O>N1C=CC=CC=1>[CH3:12][C@:13]12[CH2:30][CH2:29][C@H:28]3[C@@H:18]([CH2:19][CH2:20][C@@H:21]4[C@:26]3([CH3:27])[CH2:25][CH2:24][C@H:23]([OH:31])[CH2:22]4)[C@@H:17]1[CH2:16][CH:15]=[CH:14]2.[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])(=[O:51])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 1514495 Alpha-androst-16-en-3 beta-olHCID 441302Epiandrosterone

Product 1

HCID 86743631(3beta, 5alpha)-Androst-16-en-3-ol 4-methylbenzenesulphonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Methylbenzenesulphonyl chloride (20 g) was added to a stirred solution of (3β, 5α)-androst-16-en-3-ol (20 g), which was prepared from (3β, 5α)-androstan-3-ol- 17-one in a similar way as described in Examples 1 and 2, in pyridine (100 ml) at °C. The mixture was stirred at 0°-5° C. for 1 h., then set aside in a refrigerator for 3 d. Water was added to precipitate the product as off-white prisms. Recrystallisation from diethyl ether-methanol gave colourless prisms of (3β, 5α)-androst-16-en-3-ol 4-methylbenzenesulphonate, Which Was treated as described in Example 3.

Workup

  1. waitset aside in a refrigerator for 3 d
  2. customto precipitate the product as off-white prisms
  3. customRecrystallisation from diethyl ether-methanol

Sources & evidence

ORD record
ord-f059c78314b0476a9d87b99727989ed6
Source dataset
uspto-grants-1990_01
Patent number
US04891366

Linked notes

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