2-(Benzylamino)acetic acid → Ethyl 1-benzylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 2415650Notes

Reaction equation

HRID 2415650 reaction equation
[CH2:1]([N:4]([CH2:10][CH:11]=O)[C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH:2]=[CH2:3].[CH2:13]([NH:20][CH2:21]C(O)=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:13]([N:20]1[CH2:21][CH2:3][CH:2]2[CH:11]1[CH2:10][N:4]([C:5]([O:6][CH2:7][CH3:8])=[O:9])[CH2:1]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 869652-(Benzylamino)acetic acidHCID 11084330Ethyl allyl(2-oxoethyl)carbamate

Product 1

HCID 11086974Ethyl 1-benzylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a two-liter round bottom flask was added 81.5 g (476 mmol) of ethyl N-allyl-N-(2-oxoethyl)-carbamate (I-3c), 78.6 g (476 mmol) of N-benzylglycine (I-3d), and 1.2 liters of toluene. The reaction mixture was refluxed for 24 hours. The reaction mixture was then decanted to remove sludge residue which formed on the bottom of the flask. The decanted solution was concentrated in vacuo to a brown syrup.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. customThe reaction mixture was then decanted
  3. customto remove sludge residue which
  4. customformed on the bottom of the flask
  5. concentrationThe decanted solution was concentrated in vacuo to a brown syrup

Sources & evidence

ORD record
ord-0a7c82630b684c3f8acf56778d6414b7
Source dataset
uspto-grants-2004_11
Patent number
US06821964B2

Reaction notes

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