4-Phenylbutyric Acid → HCID 18642608, compound

HRID 703516Notes

Reaction equation

HRID 703516 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.Cl.[NH:27]1[C@H:31]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:30][C@@H:29]2[CH2:42][CH2:43][CH2:44][C@H:28]12>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([N:27]2[C@H:31]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[CH2:30][C@@H:29]3[CH2:42][CH2:43][CH2:44][C@H:28]23)=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13216857Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 18642608HCID 18642608, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4.92 g (30 mmol) of 4-phenylbutyric acid are dissolved together with 8.4 ml of triethylamine in 200 ml of dry tetrahydrofuran. While cooling in ice, 2.9 ml of ethyl chloroformate are added dropwise. After stirring at 0° C. for 1 hour, 7.4 g of benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride are added, and the mixture is stirred at room temperature for a further 12 hours. Filtration is followed by concentration, and the residue is taken up in 3% NaHCO3 /ethyl acetate. The organic phase is separated off and washed with 10% strength citric acid, 3% strength NaHCO3 solution and saturated brine, once each, dried with MgSO4 and concentrated. Chromatography on silica gel with ethyl acetate/cyclohexane (1:2) as mobile phase results in 9.05 g of the title compound as a colorless oil.

Workup

  1. temperatureWhile cooling in ice
  2. stirringthe mixture is stirred at room temperature for a further 12 hours
  3. filtrationFiltration
  4. concentrationis followed by concentration
  5. customThe organic phase is separated off
  6. washwashed with 10% strength citric acid, 3% strength NaHCO3 solution and saturated brine
  7. dry with materialonce each, dried with MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b72469dace0946a3868f4b3d0e6e705c
Source dataset
uspto-grants-1991_01
Patent number
US04983623

Reaction notes

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