Tetrabutylammonium Fluoride → HCID 57156543, compound

HRID 479312Notes

Reaction equation

HRID 479312 reaction equation
[OH:1][C@H:2]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:27])[CH2:13][CH2:14][CH2:15][C@@H:16]([CH3:26])[CH2:17][O:18][Si](C(C)(C)C)(C)C)[C:3]1([CH3:38])[CH3:37].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CO>[CH3:38][C:3]1([CH3:37])[C@@H:2]([OH:1])[CH2:34][CH2:33][C@@:32]2([CH3:35])[C:4]1=[CH:5][CH2:6][C@@H:7]1[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:27])[CH2:13][CH2:14][CH2:15][C@@H:16]([CH3:26])[CH2:17][OH:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 20599271HCID 20599271, compound

Product 1

HCID 57156543HCID 57156543, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Silyl deprotection of 3β-hydroxy-4,4-dimethyl-(25R)-26-(tert-butyldimethylsilyloxy)cholest-5-ene (60 mg, 0.11 mmol) with tetrabutyl ammonium fluoride and recrystallisation from methanol to give 4,4-dimethyl-(25R)-cholest-5-ene-3β,26-diol (30 mg).

Sources & evidence

ORD record
ord-32efab3bcf05426b9f72c40a284842cd
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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