Imidazole → HCID 11763027, compound

HRID 479310Notes

Reaction equation

[CH2:1]([OH:29])[C@@H:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].N1C=CN=C1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].CN(C)C=O>O>[Si:35]([O:29][CH2:1][C@@H:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (25R)-Cholest-5-ene-3β,26-diol (6.24 g, 15.4 mmol), imidazole (4.21 g, 61 mmol) and tert-butyldimethylsilylchloride (2.34 g, 15.4 mmol) and dimethylformamide was heated to 60° C. for 1.5 hours, then poured into water (300 ml) and extracted with diethyl ether (5×100 ml). Flash chromatography afforded (25R)-26-(tert-butyldimethylsilyloxy)cholest-5-en-3β-ol (5.09 g). Melting point: 93.5° C. The 1H-NMR spectrum (CDCl3, d) showed characteristic signals at: 0.01 (s, 6H), 0.63 (s, 3H), 0.90 (s, 9H), 3.4 (m, 3H, H-26 and H-3), 5.32 (d, 1H, H-6). The 13C-NMR spectrum (CDCl3, d) showed characteristic signals at: 50.1 (C-9), 56.1 (C14), 56.7 (C-17), 68.5 (C-26), 71.7 (C-3), 121.6 (C-6), 140.7 (C-5). The mass spectrum showed characteristic peaks at: 516.5 (M+).

Workup

extractionextracted with diethyl ether (5×100 ml)

Sources & evidence

ORD record: ord-a743553f7429414aa15a211a49b961e1
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06645953B2

Reaction notes

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