methyl (2E)-3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}prop-2-enoate → Methyl 3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}propanoate

HRID 1920784Notes

Reaction equation

HRID 1920784 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[CH3:33])[CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH2:11][C@@H:12]([OH:29])[CH2:13][O:14][C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1/[CH:23]=[CH:24]/[C:25]([O:27][CH3:28])=[O:26])[CH3:16]>C(O)C.[C].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[CH3:33])[CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH2:11][C@@H:12]([OH:29])[CH2:13][O:14][C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH3:16]

Participants

4

Reactant 1

HCID 58580652methyl (2E)-3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}prop-2-enoate

Product 1

HCID 58581208Methyl 3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}propanoateYield 90%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl (2E)-3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}prop-2-enoate (127 mg, 0.28 mmol), which had been obtained in Example 1 (1f), in ethanol (2.8 mL) was added with 10% palladium-carbon (wet, 50 wt %, 63 mg), and hydrogenated under atmospheric pressure for 3 hours. The reaction solution was filtered through Celite and washed with ethanol. The solvent was distilled off under reduced pressure to give the title compound as a colorless oily substance (115 mg, yield 90%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwashed with ethanol
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9f1906de5e60493bb69953cc6d135b1f
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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