HCID 57110447, compound → HCID 86753771, compound

HRID 1417543Notes

Reaction equation

HRID 1417543 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@@H:28]([CH2:29][OH:30])[CH2:27][CH2:26][C@@:9]32[O:13][CH2:12][C:11]([C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=2[O:22][CH:23]([CH3:25])[CH3:24])=[CH:10]3)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[C@@H:28]([CH2:29][OH:30])[CH2:27][CH2:26][C@@:9]32[O:13][CH2:12][C@H:11]([C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=2[O:22][CH:23]([CH3:25])[CH3:24])[CH2:10]3)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57110447HCID 57110447, compound

Product 1

HCID 86753771HCID 86753771, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared by hydrogenation of (5R, 6S, 7S)-6-(4-fluorophenyl)-3-(5-cyano-2-isopropoxy-phenyl)-1-oxaspiro[4.4]non-3-ene-7-methanol (78 mg) in methanol (4 mL) over 10% palladium-on-charcoal (20 mg) at 50 psi for 90 minutes. Purification was achieved by means of silica gel chromatography eluting with 10% acetone/methylene chloride; yield 35 mg.

Workup

  1. customPurification
  2. washeluting with 10% acetone/methylene chloride

Sources & evidence

ORD record
ord-271ddeffda4c4ba78e089046f9a21471
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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