MAGNESIUM SILICATE (synthetic) → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-oxopregna-5,7,16-triene

HRID 635028ノート

反応式

HRID 635028 の反応式
[Si:1]([O:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([OH:23])[CH3:22])[CH2:12][C@@H:11]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[O-][Si]([O-])=O.[Mg+2]>ClCCl>[Si:1]([O:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21](=[O:23])[CH3:22])[CH2:12][C@@H:11]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:33])[CH3:34])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 2724130Cornforth reagentHCID 120200781alpha,3beta-bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7,16-triene

生成物 1

HCID 120200821alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-oxopregna-5,7,16-triene収率 57.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A suspension of 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7,16-triene (600 mg, 1.07 mmol), pyridinium dichromate (610 mg, 1.61 mmol) and Florisil (3 g) in dichloromethane (10 ml) was stirred at room temperature for 1.5 hours, then ultrasonicated for 2.5 hours. The solvent was distilled off under reduced pressure and the resulting residue was diluted with diethyl ether and filtered through Celite. The solvent was distilled off under reduced pressure and the resulting residue was purified by column chromatography (hexane:ethyl acetate=15:1) to give the title compound as a colorless solid (343 mg, 57%).

後処理

  1. customultrasonicated for 2.5 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe resulting residue was diluted with diethyl ether
  4. filtrationfiltered through Celite
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=15:1)

出典と根拠

ORDレコード
ord-66b816cb1bd8449781b815c0faef2115
出典データセット
uspto-grants-2001_02
特許番号
US06184398B2

反応ノート

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