TBAF tetrahydrofuran → 17-(2-Ethyl-2-hydroxybutoxymethyl)-1alpha,3beta-dihydroxyandrosta-5,7,16-triene

HRID 1792210Notes

Reaction equation

HRID 1792210 reaction equation
[Si]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][O:29][CH2:30][C:31]([CH2:35][CH3:36])([OH:34])[CH2:32][CH3:33])[CH2:12][C@@H:11]([O:37][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:32]([C:31]([OH:34])([CH2:35][CH3:36])[CH2:30][O:29][CH2:28][C:20]1[C@:21]2([CH2:23][CH2:24][C@H:25]3[C:16](=[CH:15][CH:14]=[C:13]4[C@:26]3([CH3:27])[C@@H:9]([OH:8])[CH2:10][C@H:11]([OH:37])[CH2:12]4)[C@@H:17]2[CH2:18][CH:19]=1)[CH3:22])[CH3:33]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 696301361alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(2-ethyl-2-hydroxybutoxymethyl)androsta-5,7,16-triene

Product 1

HCID 6963054717-(2-Ethyl-2-hydroxybutoxymethyl)-1alpha,3beta-dihydroxyandrosta-5,7,16-trieneYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-{2-ethyl-2-hydroxybutoxymethyl}androsta-5,7,16-triene (139 mg, 0.216 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (1.3 ml, 1.3 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (4 hours), worked up and the thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), dichloromethane:ethanol=10:1, developed three times) to give the titled compound (64.4 mg, 72%) as a colorless oil.

Workup

  1. customof Example 5(2) (4 hours)
  2. customthe thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), dichloromethane:ethanol=10:1, developed three times)

Sources & evidence

ORD record
ord-a773ccc2032d4a18904f46db6e89d973
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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