Androstane-3beta,5alpha,17beta-triol → HCID 14135097, compound

HRID 42083Notes

Reaction equation

HRID 42083 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@:10]4([OH:21])[C@:15]3([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:22]>CS(C)=O>[OH:21][C@:10]12[CH2:11][C:12](=[O:20])[CH2:13][CH2:14][C@:15]1([CH3:16])[C@@H:17]1[C@H:7]([C@H:6]3[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[C:3](=[O:22])[CH2:4][CH2:5]3)[CH2:8][CH2:9]2

Participants

3

Reactant 1

HCID 14135090Androstane-3beta,5alpha,17beta-triol

Product 1

HCID 14135097HCID 14135097, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of androstane-3β,5α,17β-triol (0.48 g) and IBX (0.72 g) in DMSO (8 mL) was stirred at −15° C. overnight and then quenched at room temperature by addition of H2O (40 mL). After stirring for 15 min, the mixture was filtered and the cake was washed with EtOAc. The layers were separated, and the aqueous phase was extracted with EtOAc (3×40 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20) to give the title compound II-aa (0.36 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.48 (1H, s), 2.72 (1H, d), 2.60-1.18 (20H, m), 1.23 (3H, s), 0.86 (3H, s).

Workup

  1. customquenched at room temperature by addition of H2O (40 mL)
  2. filtrationthe mixture was filtered
  3. washthe cake was washed with EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×40 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)

Sources & evidence

ORD record
ord-31822fd4df274848ae06522671e37093
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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