Quinoline → 1alpha,3beta-dihydroxy-17-{4-hydroxy-4-methyl-(2Z)-pentenyloxymethyl}androsta-5,7,16-triene

HRID 1792211Notes

Reaction equation

HRID 1792211 reaction equation
[OH:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH:8]=[C:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH:12]=[C:13]2[CH2:21][O:22][CH2:23][C:24]#[C:25][C:26]([OH:29])([CH3:28])[CH3:27])[CH2:5][C@@H:4]([OH:30])[CH2:3]1.N1C2C(=CC=CC=2)C=CC=1>[Pd].CO>[OH:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH:8]=[C:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH:12]=[C:13]2[CH2:21][O:22]/[CH:23]=[CH:24]\[CH2:25][C:26]([OH:29])([CH3:28])[CH3:27])[CH2:5][C@@H:4]([OH:30])[CH2:3]1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 696296971alpha,3beta-Dihydroxy-17-(4-hydroxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-triene

Product 1

HCID 867601541alpha,3beta-dihydroxy-17-{4-hydroxy-4-methyl-(2Z)-pentenyloxymethyl}androsta-5,7,16-trieneYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1α,3β-Dihydroxy-17-(4-hydroxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-triene (78 mg, 0.189 mmol), quinoline (12.3 mg, 0.0952 mmol), 5% palladium/barium sulfate (16 mg) and methanol (5 ml) were stirred at room temperature for 2 hours under a hydrogen atmosphere. The reaction mixture was filtered, evaporated for remove the solvent and purified by column chromatography (dichloromethane: methanol=20:1) to give the titled compound (61 mg, 78%) as a colorless glassy substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customfor remove the solvent
  4. custompurified by column chromatography (dichloromethane: methanol=20:1)

Sources & evidence

ORD record
ord-e66355c7f5344561854354458ec36a7e
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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