Sodium Bicarbonate → HCID 11772697, compound

HRID 895840Notes

Reaction equation

HRID 895840 reaction equation
[CH3:1][C:2]1([CH3:26])[C@@H:22]([OH:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[CH:3]1[CH2:4][CH2:5][C:6]1[C:7]3[C@:15]([CH3:25])([CH2:16][CH2:17][C:18]=12)[C@@H:10]([C@H:11]([CH3:14])[CH2:12][OH:13])[CH2:9][CH:8]=3.C(=O)(O)[O-].[Na+]>ClCCl>[OH:23][C@H:22]1[CH2:21][CH2:20][C@@:19]2([CH3:24])[CH:3]([CH2:4][CH2:5][C:6]3[C:7]4[C@:15]([CH3:25])([CH2:16][CH2:17][C:18]=32)[C@@H:10]([C@H:11]([CH3:14])[CH:12]=[O:13])[CH2:9][CH:8]=4)[C:2]1([CH3:1])[CH3:26]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69283450HCID 69283450, compound

Product 1

HCID 11772697HCID 11772697, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g (20S)-4,4,20-trimethyl-pregna-8,14-dien-3β,21-diol in 10 ml dichloromethane 5.4 ml of a 0.5 M Dess-Martin-Periodinane solution were added at room temperature. The mixture was stirred for one hour, poured into saturated sodium bicarbonate solution, extracted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 230 mg (20S)-3β-hydroxy-4,4,20-trimethyl-pregna-8,14-dien-21-al as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d98242312ce7404ca37d2e755f2d56fe
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

Loading…