Imidazole → HCID 67856976, compound

HRID 1587025Notes

Reaction equation

HRID 1587025 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:11]2=[O:22])[CH2:3]1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CN=C1>CN(C)C1C=CN=CC=1.CN(C)C=O.CCOCC>[Si:23]([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:11]2=[O:22])[CH2:3]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22295513HCID 22295513, compound

Product 1

HCID 67856976HCID 67856976, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3α, 12α-dihydroxy-5β-androstan-17-one (4.29 g), tert-butyldimethylsilyl chloride (3.26 g), 4-dimethylaminopyridine (0.17 g) and imidazole (1.9 g) in dimethylformamide (38 ml) is stirred at room temperature for about 1 hour, diluted with ether and washed with water. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product which is used, without further treatment, for the next step.

Workup

  1. washwashed with water
  2. dry with materialThe organic solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28d2d79883ac4fa395fa920a7ace0c87
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

Loading…