Pyridinium → HCID 86748908, compound

HRID 1735742Notes

Reaction equation

HRID 1735742 reaction equation
[NH+]1C=CC=CC=1.[OH:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@:14]3([OH:29])[CH2:15][CH2:16][C@@H:17]2[CH:27]=[O:28])[CH2:9]1>ClCCl.C(OCC)C>[O:7]=[C:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@:14]3([OH:29])[CH2:15][CH2:16][C@@H:17]2[CH:27]=[O:28])[CH2:9]1

Participants

5

Reactant 2

HCID 4989215PyridiniumHCID 109033043beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehyde

Product 1

HCID 86748908HCID 86748908, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 0.88 g of pyridinium dicromate in 2.2 ml of dichloromethane a solution of 0.50 g of 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde (Boutagy J. and Thomas R., Aust. J. Chem., 1971, 24, 2723) in 2.5 ml of dichloromethane was added at room temperature. After 20 hrs the mixture was diluted with diethyl ether and filtered through celite; the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 6/4 as eluant; the fractions containing the title compound were collected and evaporated to give 0.30 g of the title compound (II-e) as a white foam.

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered through celite
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe crude product was purified by flash-chromatography (SiO2)
  5. additionthe fractions containing the title compound
  6. customwere collected
  7. customevaporated

Sources & evidence

ORD record
ord-480f0e896c874bd8aec6782c4f7528c3
Source dataset
uspto-grants-1996_07
Patent number
US05538960

Reaction notes

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