Quinoline → 17-{4-ethyl-4-hydroxy-(2Z)-hexenyloxymethyl}-1alpha,3beta-dihydroxyandrosta-5,7,16-triene

HRID 1792212Notes

Reaction equation

HRID 1792212 reaction equation
[CH2:1]([C:3]([OH:32])([CH2:30][CH3:31])[C:4]#[C:5][CH2:6][O:7][CH2:8][C:9]1[C@:10]2([CH2:27][CH2:26][C@H:25]3[C:15](=[CH:16][CH:17]=[C:18]4[C@:23]3([CH3:24])[C@@H:22]([OH:28])[CH2:21][C@H:20]([OH:29])[CH2:19]4)[C@@H:12]2[CH2:13][CH:14]=1)[CH3:11])[CH3:2].N1C2C(=CC=CC=2)C=CC=1>[Pd].CO>[CH2:1]([C:3]([OH:32])([CH2:30][CH3:31])[CH2:4]/[CH:5]=[CH:6]\[O:7][CH2:8][C:9]1[C@:10]2([CH2:27][CH2:26][C@H:25]3[C:15](=[CH:16][CH:17]=[C:18]4[C@:23]3([CH3:24])[C@@H:22]([OH:28])[CH2:21][C@H:20]([OH:29])[CH2:19]4)[C@@H:12]2[CH2:13][CH:14]=1)[CH3:11])[CH3:2]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 6963081717-(4-Ethyl-4-hydroxy-2-hexynyloxymethyl)-1alpha,3beta-dihydroxyandrosta-5,7,16-triene

Product 1

HCID 8676015517-{4-ethyl-4-hydroxy-(2Z)-hexenyloxymethyl}-1alpha,3beta-dihydroxyandrosta-5,7,16-triene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The fraction (0.3 g) containing 17-(4-ethyl-4-hydroxy-2-hexynyloxymethyl)-1α,3β-dihydroxyandrosta-5,7,16-triene obtained in Example 11 (2), 5% palladium/barium sulfate (0.3 g), quinoline (0.03 ml, 0.2538 mmol) and methanol (6.8 ml) were subjected to reaction using a procedure similar to that of Example 29(1) (4 hours) and worked up to give a mixture (0.80 mg) containing the targeted compound.

Workup

  1. customwere subjected to reaction
  2. customof Example 29(1) (4 hours)

Sources & evidence

ORD record
ord-9953d635993c4e47977430099ff37e58
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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