Tetrahydrofuran → 1alpha-(tert-Butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(2-hydroxy-2-methylpropylthio)pregna-5,7,16-triene

HRID 1268497Notes

Reaction equation

HRID 1268497 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][C:24](OC2C=CC=CC=2)=O)[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:41][C:42]1([O:45]C1)[CH3:43].O1CCCC1.[OH-].[K+]>CO>[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24][C:42]([OH:45])([CH3:43])[CH3:41])[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11208Isobutylene oxideHCID 14797Potassium HydroxideHCID 12019512HCID 12019512, compound

Product 1

HCID 120195161alpha-(tert-Butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(2-hydroxy-2-methylpropylthio)pregna-5,7,16-trieneYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under the same conditions as in Example 3, 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-phenoxycarbonylthiopregna-5,7,16-triene (83.0 mg, 0.143 mmol), isobutylene oxide (113 mg, 1.56 mmol), tetrahydrofuran (0.5 ml) and 1M KOH solution in methanol (0.5 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, hexane:ethyl acetate=1:1, developed once) to give the title compound as a colorless oil (62.3 mg, 82%).

Workup

  1. customthe residue was purified by preparative thin layer chromatography (0.5 mm×2, hexane

Sources & evidence

ORD record
ord-51baa25390fd4afb8718f0ce468b7f73
Source dataset
uspto-grants-2003_04
Patent number
US06555699B2

Reaction notes

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