Pyridine → HCID 15251367, compound

HRID 1938159Notes

Reaction equation

HRID 1938159 reaction equation
[CH3:1][C:2]([C@:4]1([OH:25])[C@@:8]2([CH3:24])[CH2:9][C@H:10]([OH:23])[C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[C:26]([O:23][C@H:10]1[CH2:9][C@@:8]2([CH3:24])[C@@H:7]([CH2:6][CH2:5][C@:4]2([OH:25])[C:2](=[O:3])[CH3:1])[C@H:12]2[C@H:11]1[C@:21]1([CH3:22])[C:15]([CH2:14][CH2:13]2)=[CH:16][C:17](=[O:18])[CH2:19][CH2:20]1)(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9282721-Desoxycortisol

Product 1

HCID 15251367HCID 15251367, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-pregnene-11β,17α-diol-3,20-dione (2) (2 g), acetic anhydride (10 ml), pyridine (20 ml) and 4-dimethylaminopyridine (20 mg) was stirred for 6 hours at room temperature. The reaction mixture was diluted with water (50 ml) and extracted with chloroform. The chloroform layer was sequentially washed with 10% HCl, a 5% aqueous NaHCO3 solution, and brine, dried over Na2SO4, and concentrated. The residue was subjected to column chromatography (silica gel, 150 g) using 70% chloroform/hexane as eluant, thereby obtaining an acetylated derivative (3) (2.24 g, 100%). Recrystallization from ethyl acetate/hexane afforded white crystals having a melting point of 159.5°-160° C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was sequentially washed with 10% HCl
  3. dry with materiala 5% aqueous NaHCO3 solution, and brine, dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6676c4c861b4630947ac77225f1cdaf
Source dataset
uspto-grants-1997_12
Patent number
US05693629

Reaction notes

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