Phenethylamine → (S)-2-Oxo-5-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1668419Notes

Reaction equation

HRID 1668419 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[CH2:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]1[C@H:12]([C:17](=[O:19])[NH:39][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:13][CH2:14][C:15]1=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

Product 1

HCID 57612752(S)-2-Oxo-5-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

(S)-5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (14.9 g, 57 mmol) is suspended in dichloromethane (100 mL) and added DMAP (7.1 g, 58 mmol) while cooling on ice (0-5° C.). The suspension immediately clarified. EDCI (11.1 g, 58 mmol) is added resulting in precipitation which quickly clarified again. Phenethylamine (6.8 mL, 54 mmol) is added slowly via syringe. The reaction is complete in one half hour. The dichloromethane layer is washed with aqueous 10% citric acid, water and saturated bicarb, then dried over anhydrous sodium sulfate, filtered and concentrated to a white solid. LCMS characterization ES+367.1 (m+1).

Workup

  1. customresulting in precipitation which
  2. waitThe reaction is complete in one half hour
  3. washThe dichloromethane layer is washed with aqueous 10% citric acid, water and saturated bicarb
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-4f1e8a73cb34449180ba72306e66a5ab
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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