4-(2-Oxopyrrolidin-1-yl)benzoic acid → Trans-4-(2-oxo-pyrrolidin-1-yl)cyclohexanecarboxylic acid

HRID 2116763Notes

Reaction equation

HRID 2116763 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]>[C].[Rh].CO>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([C:11]([OH:13])=[O:12])[CH2:14][CH2:15]2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]

Participants

4

Reactant 1

HCID 7731304-(2-Oxopyrrolidin-1-yl)benzoic acid

Product 1

HCID 11572026Trans-4-(2-oxo-pyrrolidin-1-yl)cyclohexanecarboxylic acidYield 468.5%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 887MethanolSolvent

Procedure

4-(2-Pyrrolidon-1-yl)benzoic acid (4.0 g, 0.0195 mol), 5% rhodium-carbon catalyst (6.89 g, 1.5% mol) and methanol (200 mL) are charged in an autoclave (300 mL) and stirred at room temperature for 24 hours under hydrogen pressure (9 atm, conversion rate>99%, cis:trans=75:25). The reaction solution is concentrated to 100 ml, adjusted to pH 2 with conc. hydrochloric acid (11 g), and extracted with chloroform (100 mL) (×3). The organic layers are combined, washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting crystals are collected with toluene, and air-dried at 50° C. overnight to give 4-(2-pyrrolidon-1-yl)cyclohexylcarboxylic acid (19.3 g, 93.7%, cis:trans=65:35).

Workup

  1. concentrationThe reaction solution is concentrated to 100 ml
  2. extractionextracted with chloroform (100 mL) (×3)
  3. washwashed with saturated brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crystals are collected with toluene
  7. customair-dried at 50° C. overnight

Sources & evidence

ORD record
ord-e5dccca098984eefb623997c5150f6c6
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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