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Aniline → (S)-1-benzyloxycarbonyl-N-phenyl-2-pyrrolidinecarboxamide

HRID 980391
Notes
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Reaction equation

HRID 980391 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 12859188(S)-1-benzyloxycarbonyl-N-phenyl-2-pyrrolidinecarboxamideYield 80.1%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

In 50 ml of THF was dissolved 4.99 g of N-benzyloxycarbonyl-L-proline (20) and after adding thereto 2.23 g of triethylamine and 2.39 g of ethyl chloroformate, the reaction was maintained for 20 minutes under ice-cooling. To the reaction mixture was added 2.79 g of aniline and the reaction was performed for one hour under ice-cooling. The solvent was distilled off, the residue thus formed was dissolved in ethyl acetate, and the solution was washed, in succession, with an aqueous solution of 1N hydrochloric acid, a saturated aqueous sodium hydrogen, carbonate solution, and then a saturated aqueous sodium chloride solution. The organic layer thus formed was dried by anhydrous sodium sulfate and then concentrated to dryness. The residue was recrystallized from chloroform-ethyl acetate-hexane to provide 5.20 g of (S)-1-benzyloxycarbonyl-N-phenyl-2-pyrrolidinecarboxamide (93) having a melting point of 143°-144° C.

Workup

  1. additionafter adding
  2. temperaturecooling
  3. temperaturecooling
  4. distillationThe solvent was distilled off
  5. customthe residue thus formed
  6. washthe solution was washed, in succession, with an aqueous solution of 1N hydrochloric acid
  7. customThe organic layer thus formed
  8. dry with materialwas dried by anhydrous sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe residue was recrystallized from chloroform-ethyl acetate-hexane

Sources & evidence

ORD record
ord-0dc3b81adada4beea55f1de9f2dcad9f
Source dataset
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04636567

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes