Imidazole → HCID 11271717, compound

HRID 895837Notes

Reaction equation

HRID 895837 reaction equation
OC[CH2:3][CH2:4][C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1.N1C=CN=[CH:26]1.[CH:30]([Si:33](Cl)([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])([CH3:32])[CH3:31].[OH2:41]>ClCCl>[CH:30]([Si:33]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[O:41][CH2:3][C@H:4]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)[CH3:26])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 54191709HCID 54191709, compound

Product 1

HCID 11271717HCID 11271717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30 g of (20S)-20-[(hydroxymethyl]-pregna-4-en-3-one and 13.5 g imidazole in 300 ml dichloromethane 26 ml of triisopropylsilylchloride were added dropwise at room temperature. The reaction mixture was stirred for 20 hours at the same temperature and then poured into water. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 45.4 g of crude (20S)-20-[((triisopropylsilyl)oxy)methyl]-pregna-4-en-3-one as a brown oil, which was used without further purification.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6e5d96dc336434fa070aa6341be436e
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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