(E)-3beta,14beta-dihydroxy-5beta-pregn-20-ene-21-carboxaldehyde → 3-(3beta,14beta-Dihydroxy-5beta-androstane-17beta-yl)propionaldehyde

HRID 1080639Notes

Reaction equation

HRID 1080639 reaction equation
[OH:1][C@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:24])[C@:8]3([OH:25])[CH2:9][CH2:10][C@@H:11]2/[CH:12]=[CH:13]/[CH:14]=[O:15])[CH2:3]1>[Pd].C(O)C>[OH:1][C@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:24])[C@:8]3([OH:25])[CH2:9][CH2:10][C@@H:11]2[CH2:12][CH2:13][CH:14]=[O:15])[CH2:3]1

Participants

4

Reactant 1

HCID 10736377(E)-3beta,14beta-dihydroxy-5beta-pregn-20-ene-21-carboxaldehyde

Product 1

HCID 105938883-(3beta,14beta-Dihydroxy-5beta-androstane-17beta-yl)propionaldehydeYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6.00 g of (E)-3β,14β-dihydroxy-5β-pregn-20-ene-21-carboxaldehyde (Fullerton D. S. and Pankaskie M. C., J. Med. Chem., 1976, 19, 1330) and 1.20 g of 5% palladium on charcoal in 1.20 l of ethanol was hydrogenated at room temperature and atmospheric pressure for 30 min. The mixture was then filtered through Celite and ethanol was evaporated to dryness to give 5.95 g of the title compound (II-c) as a white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was then filtered through Celite and ethanol
  3. customwas evaporated to dryness

Sources & evidence

ORD record
ord-f93a1f1b177942588d823997eb6ae89a
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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