Hydrochloric Acid → HCID 54362083, compound

HRID 2050942Notes

Reaction equation

HRID 2050942 reaction equation
C([O:3][C:4]1[CH2:5][C@@H:6]([CH2:11][C@H:12]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15](=O)[CH2:14][CH2:13]2)[CH2:7][C:8](=[O:10])[CH:9]=1)C.C1(CN2CCCC2=[O:37])C=CC=CC=1.Cl>O1CCCC1>[O:37]=[C:13]1[CH2:14][CH2:15][N:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:12]1[CH2:11][CH:6]1[CH2:5][C:4](=[O:3])[CH2:9][C:8](=[O:10])[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 791761-Benzyl-3-pyrrolidoneHCID 10245891HCID 10245891, compound

Product 1

HCID 54362083HCID 54362083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (5S,1R)-5-[(3-ethoxy-5-oxo-3-cyclohexen-1-yl)methyl]-1-(phenylmethyl)-2-pyrrolidinone and (5S,1S)-5-[(3ethoxy-5-oxo-3-cyclohexen-1-yl)methyl[-1-(phenylmethyl)-2-pyrrolidinone (150 mg, 0.46 mmol) in 10 mL of tetrahydrofuran was treated with 2 mL of 2N HCl and stirred at room temperature for 2 h, then refluxed for 1 h. The solvent was removed on a rotary evaporator and the residue was extracted with methylene chloride. The combined extracts were dried over Na2SO4 and evaporated to give 130 mg of (S)-5-[[oxo-1-(phenylmethyl)-2-pyrrolidinyl]methyl]-1,3-cyclohexanedione, mp 159°-161° C. (ethyl acetate), which was identical in all respects to that obtained in the synthesis from (E)-4-[2(S)-5-oxo-1-(phenylmethyl)-2-pyrrolidinyl]-2-butenoic acid, ethyl ester.

Workup

  1. temperaturerefluxed for 1 h
  2. customThe solvent was removed on a rotary evaporator
  3. extractionthe residue was extracted with methylene chloride
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ab1faecc03cc46ada29cbe9527794939
Source dataset
uspto-grants-1991_05
Patent number
US05015653

Reaction notes

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