HCID 67422430, compound → HCID 67422772, compound

HRID 1920790Notes

Reaction equation

HRID 1920790 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([C@H:16]([O:18][CH2:19][C@H:20]([OH:36])[CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][C@H:23]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([F:35])[CH:29]=2)[CH3:17])[CH:3]=1>C(O)C.[Rh]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([C@H:16]([O:18][CH2:19][C@H:20]([OH:36])[CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][C@H:23]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([F:35])[CH:29]=2)[CH3:17])[CH:3]=1

Participants

4

Reactant 1

HCID 67422430HCID 67422430, compound

Product 1

HCID 67422772HCID 67422772, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl (2E)-3-{4-chloro-5-fluoro-2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}prop-2-enoate (320 mg, 0.61 mmol) which had been obtained in Example 156 (156a) was dissolved in ethanol (20 mL), added with rhodium/alumina (96 mg), and stirred at room temperature for 45 minutes under a hydrogen atmosphere. The reaction solution was filtered through Celite. The solvent was distilled off under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane/ethyl acetate=1/1) to give the title compound as a colorless oily substance (310 mg, yield 97%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. distillationThe solvent was distilled off under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-b1aa4c936a07459e8e185d693d047a83
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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