1-Bromo-5-triethylsilyloxy-5-methylhexane → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(5-triethylsilyloxy-5-methylhexylthiomethyl)androsta-5,7,16-triene

HRID 1792215Notes

Reaction equation

HRID 1792215 reaction equation
[C:1]([S:4][CH2:5][C:6]1[C@:7]2([CH2:24][CH2:23][C@H:22]3[C:12](=[CH:13][CH:14]=[C:15]4[C@:20]3([CH3:21])[C@@H:19]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:18][C@H:17]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:16]4)[C@@H:9]2[CH2:10][CH:11]=1)[CH3:8])(=O)[CH3:2].BrCC[CH2:44][CH2:45][C:46]([O:49][Si:50]([CH2:55][CH3:56])([CH2:53][CH3:54])[CH2:51][CH3:52])([CH3:48])[CH3:47].CO.[OH-].[K+]>O1CCCC1>[Si:26]([O:25][C@@H:19]1[C@@:20]2([CH3:21])[C:15](=[CH:14][CH:13]=[C:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:7]2([CH3:8])[C@H:9]3[CH2:10][CH:11]=[C:6]2[CH2:5][S:4][CH2:1][CH2:2][CH2:44][CH2:45][C:46]([O:49][Si:50]([CH2:55][CH3:56])([CH2:51][CH3:52])[CH2:53][CH3:54])([CH3:47])[CH3:48])[CH2:16][C@@H:17]([O:33][Si:34]([C:37]([CH3:39])([CH3:40])[CH3:38])([CH3:35])[CH3:36])[CH2:18]1)([C:29]([CH3:30])([CH3:32])[CH3:31])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 220168031-Bromo-5-triethylsilyloxy-5-methylhexaneHCID 23689386Potassium hydroxide methanolHCID 8658997017-Acetylthiomethyl-1alpha,3beta-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene

Product 1

HCID 696297051alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(5-triethylsilyloxy-5-methylhexylthiomethyl)androsta-5,7,16-trieneYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17-Acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene (262 mg, 0.434 mmol), 1-bromo-5-triethylsilyloxy-5-methylhexane (266 mg, 0.860 mmol), a 1M potassium hydroxide methanol solution (3 ml) and tetrahydrofuran (2 ml) were subjected to reaction using a procedure similar to that of Example 31(1) (3 hours at room temperature), worked up and purified by column chromatography (hexane:toluene=4:1) to give the titled compound (320 mg, 93%) as a colorless oil.

Workup

  1. customof Example 31(1) (3 hours at room temperature)
  2. custompurified by column chromatography (hexane:toluene=4:1)

Sources & evidence

ORD record
ord-e6735f5f88fa44dda823410e416ee3fd
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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