Dichloromethane → HCID 68732269, compound

HRID 1182879Notes

Reaction equation

HRID 1182879 reaction equation
C([O:4][C:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[C:6]=1[CH2:28][CH3:29])(=O)C.C1C=C(Cl)C=C(C(OO)=[O:38])C=1.C(Cl)Cl>C(OC(C)C)(C)C.CO>[OH:38][C@@H:8]1[C:7]2[C@:20]([CH3:23])([CH2:21][CH2:22][C:5](=[O:4])[C:6]=2[CH2:28][CH3:29])[C@@H:19]2[C@H:10]([C@H:11]3[C@@:15]([CH2:17][CH2:18]2)([CH3:16])[C@@H:14]([O:24][C:25](=[O:27])[CH3:26])[CH2:13][CH2:12]3)[CH2:9]1.[OH:38][C@H:8]1[C:7]2[C@:20]([CH3:23])([CH2:21][CH2:22][C:5](=[O:4])[C:6]=2[CH2:28][CH3:29])[C@@H:19]2[C@H:10]([C@H:11]3[C@@:15]([CH2:17][CH2:18]2)([CH3:16])[C@@H:14]([O:24][C:25](=[O:27])[CH3:26])[CH2:13][CH2:12]3)[CH2:9]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 68731244HCID 68731244, compound

Product 2

HCID 68732269HCID 68732269, compoundYield 105%HCID 68733032HCID 68733032, compound

Reagents, catalysts & solvents 1

HCID 21882575Diisopropylether methanolSolvent

Procedure

To a stirred solution of 3,17β-diacetoxy-4-ethylandrosta-3,5-diene (1.08 g) in EtOH/H2O 95/5 (13.7 ml), mCPBA (1.0 g) was added. After 8 h at RT, DCM (150 ml) was added and the mixture was washed with 10% Na2SO3 aqueous solution, 5% aqueous NaHCO3 solution, and brine. The organic phase was dried over Na2SO4, and evaporated to dryness. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40) to give a mixture 6α-hydroxy-17β-acetoxy-4-ethylandrost-4-en-3-one and 6β-hydroxy-17β-acetoxy-4-ethylandrost-4-en-3-one (0.53 g, 52%).

Workup

  1. washthe mixture was washed with 10% Na2SO3 aqueous solution, 5% aqueous NaHCO3 solution, and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude reaction mixture
  5. customwas purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40)

Sources & evidence

ORD record
ord-2df9d43d3e734df783eafd6d816ec479
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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