3,3-(Ethylenedioxy)-4,4-dimethyl-6alpha-hydroxymethyl-17beta-tert-butyl-dimethylsilyloxyandrostan-7-one → 4,4-Dimethyl-6alpha-hydroxymethyl-7alpha,17beta-dihydroxyandrostan-3-one
Reaction equation
C1CO[C:3]2([CH2:20][CH2:19][C@@:18]3([CH3:21])[CH:5]([C@@H:6]([CH2:31][OH:32])[C:7](=[O:30])[C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C@@H:12]3[O:22][Si](C(C)(C)C)(C)C)[C:4]2([CH3:34])[CH3:33])[O:2]1>CO>[CH3:33][C:4]1([CH3:34])[C:3](=[O:2])[CH2:20][CH2:19][C@@:18]2([CH3:21])[CH:5]1[C@@H:6]([CH2:31][OH:32])[C@@H:7]([OH:30])[C@@H:8]1[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]1[CH2:10][CH2:11][C@@H:12]2[OH:22]Participants
3
Procedure
To a stirred solution of 3,3-(ethylenedioxy)-4,4-dimethyl-6α-hydroxymethyl-17β-tert-butyldimethylsilyloxyandrostan-7-one (Preparation 9—Step 5, 1.0 g) in MeOH (40 ml) NaBH4 (140 mg) was added at 0° C. and the mixture was warmed to RT. After 1 h the mixture was quenched by addition of 5% NaH2PO4 and extracted with DCM. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was dissolved in dioxane (20 ml) and 1N HCl (10 ml) was added. The resulting mixture was stirred at RT for 1 h and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/AcOEt 25/75) to give 4,4-dimethyl-6α-hydroxymethyl-7α,17β-dihydroxyandrostan-3-one in 76% yield.
Workup
- customAfter 1 h the mixture was quenched by addition of 5% NaH2PO4
- extractionextracted with DCM
- washThe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- customevaporated to dryness
- dissolutionThe residue was dissolved in dioxane (20 ml)
- addition1N HCl (10 ml) was added
- customevaporated to dryness
- customThe residue was purified by flash chromatography (SiO2, n-hexane/AcOEt 25/75)
Sources & evidence
- ORD record
- ord-a7dc4bab347f4a5cb6bd3b01a8135d07
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664210B2
Reaction notes
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