Imidazole → HCID 18652195, compound

HRID 1587027Notes

Reaction equation

HRID 1587027 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][C@H:14]([OH:21])[C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH:22]([CH3:38])[CH2:23][CH:24]=[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:3]1.N1C=CN=C1.[C:44]([Si:48](Cl)([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([CH3:47])([CH3:46])[CH3:45]>CN(C)C1C=CN=CC=1.CN(C)C=O.CCOCC.CCCCCC>[Si:48]([O:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][C@H:14]([OH:21])[C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH:22]([CH3:38])[CH2:23][CH:24]=[C:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:3]1)([C:44]([CH3:47])([CH3:46])[CH3:45])([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 86746916HCID 86746916, compound

Product 1

HCID 18652195HCID 18652195, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To a mixture of 3α, 12α-dihydroxy-17β-[(1,1-diphenyl)-1-penten-4-yl]-5β-androstane (10.2 g), imidazole (1.64 g) and 4-dimethylaminopyridine (0.256 g) in dimethylformamide (30 ml) is added tert-butylchlorodiphenylsilane (6.04 g) and the mixture stirred for about 3.5 hours and diluted with ether/hexane (1:1). The solution is washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in 50% ether in hexane to give the desired product.

Workup

  1. washThe solution is washed with saturated sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography in 50% ether in hexane

Sources & evidence

ORD record
ord-d2019594b6e84034b28874564ac88528
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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