Tetrahydrofuran → HCID 68730133, compound
Reaction equation
[CH2:1]1[CH2:26][O:25][C:3]2([CH2:20][CH2:19][C@@:18]3([CH3:21])[C:5](=[CH:6][CH2:7][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[OH:22])[C:4]2([CH3:24])[CH3:23])[O:2]1.C1C[O:30]CC1>>[CH2:26]1[CH2:1][O:2][C:3]2([CH2:20][CH2:19][C@@:18]3([CH3:21])[C@@:5]([OH:30])([CH2:6][CH2:7][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[OH:22])[C:4]2([CH3:24])[CH3:23])[O:25]1Participants
Procedure
To a stirred solution of 3,3-ethylenedioxy-4,4-dimethyl-5-androsten-17β-ol (190 mg) in THF (3.5 ml) at 0° C., under N2, 1M BH3.THF complex in THF (3.3 ml) was added in five portions over 5 days. The reaction mixture was cautiously quenched by dropwise addition of H2O at 0° C. (1.5 ml), followed by 4N NaOH (0.16 ml) and by 30-32 wt. % H2O2 solution in water (0.056 ml). After 24 h, EtOAc and brine were added, the phases were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, n-hexane/DCM/acetone 80/10/10) to give 3,3-ethylenedioxy-4,4-dimethylandrostan-5α,17β-diol (80 mg, 23%).
Workup
- customThe reaction mixture was cautiously quenched by dropwise addition of H2O at 0° C. (1.5 ml)
- additionEtOAc and brine were added
- customthe phases were separated
- extractionthe aqueous phase was extracted with EtOAc
- washThe combined organic extracts were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated to dryness
- customThe crude product was purified by flash chromatography (SiO2, n-hexane/DCM/acetone 80/10/10)
Sources & evidence
- ORD record
- ord-538ed74d41124632b573ec6eb4e1d21e
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664210B2
Reaction notes
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