HCID 11266833, compound → 3beta,17beta-Dihydroxyandrostan-6-one

HRID 1912669Notes

Reaction equation

HRID 1912669 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][C@H:9]([OH:21])[CH:10]4[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]>C(Cl)Cl.CC(C)=O.O=[Mn]=O>[OH:20][C@H:12]1[CH2:13][CH2:14][C@@:15]2([CH3:16])[CH:10]([C:9](=[O:21])[CH2:8][C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C@@H:3]2[OH:22])[CH2:11]1

Participants

4

Reactant 1

HCID 11266833HCID 11266833, compound

Product 1

HCID 121589203beta,17beta-Dihydroxyandrostan-6-oneYield 30%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

To a solution of androstane-3β,6α,17β-triol (3.00 g) in CH2Cl2/acetone/—H2O (300/150/6 mL), activated MnO2 (30.0 g, 345 mmol) was added in three portions over 8 h. The mixture was stirred at 45° C. overnight. After cooling to room temperature, the mixture was filtered through Celite. The filtrate was evaporated and the residue was purified by flash chromatography (SiO2, CH2Cl2/n-n-hexane/i-PrOH 10/5/1) to give 3β,17β-dihydroxyandrostan-6-one (0.89 g, 30%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.54 (d, 1H), 4.48 (d, 1H), 3.45 (m, 1H), 3.30 (m, 1H), 2.27 (dd, 1H), 2.08-0.90 (m, 19H), 0.62 (s, 3H), 0.61 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. customThe filtrate was evaporated
  4. customthe residue was purified by flash chromatography (SiO2, CH2Cl2/n-n-hexane/i-PrOH 10/5/1)

Sources & evidence

ORD record
ord-70bf88ebabb449309f18e4c81294c48e
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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