Hydrochloric Acid → (E)-3-((S)-4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester hydrochloride

HRID 549371Notes

Reaction equation

HRID 549371 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=1)=O)(C)(C)C.[ClH:25].C(OCC)C>O1CCOCC1>[ClH:25].[CH3:24][O:23][C:21](=[O:22])/[CH:20]=[CH:19]/[C:16]1[CH:17]=[CH:18][C:13]([C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57899218(S)-2-[4-((E)-2-methoxycarbonyl-vinyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67158659(E)-3-((S)-4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (S)-2-[4-((E)-2-methoxycarbonyl-vinyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (40.2 g, 115 mmol) was added 120 mL of 4 N hydrochloric acid in dioxane and the reaction mixture was stirred for 16 h. Diethyl ether (500 mL) was added to the suspension and the resulting solid was filtered and washed twice with diethyl ether to yield 29.0 g (94%) of the title compound as a white solid.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed twice with diethyl ether

Sources & evidence

ORD record
ord-300031972bc14c1a81f79ffe3e0d3e01
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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