Water → HCID 11386782, compound
Reaction equation
[CH3:1][C:2]1([CH3:36])[C:32](=[O:33])[CH2:31][CH2:30][C@@:29]2([CH3:34])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:35])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C@@H:11]([CH2:13][O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:36][C:2]1([CH3:1])[C@@H:32]([OH:33])[CH2:31][CH2:30][C@@:29]2([CH3:34])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:35])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C@@H:11]([CH2:13][O:14][Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:22]([CH3:23])[CH3:24])[CH3:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 27.3 g (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3-one in 500 ml tetrahydrofuran 1.24 g of lithiumaluminum hydride were added cautiously in small portions at room temperature. The reaction mixture was stirred for one hour and then cooled to 0□C. 2.5 ml water, 2.5 ml of a 1 N sodium hydroxide solution and 7.5 ml of water were added successively. The mixture was filtered over celite. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to give 18.2 g (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol as a pale yellow solid.
Workup
- temperaturecooled to 0□C
- filtrationThe mixture was filtered over celite
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-51dbd29686fc4c0e99084697e27ea708
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06916921B2
Reaction notes
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