Benzylamine → cis-1-Benzyl-5-(N-benzylcarbamoyl)-pyrrolidine-2-carboxylic acid

HRID 1743699Notes

Reaction equation

HRID 1743699 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N:16]1[CH:21]2[CH2:22][CH2:23][CH:17]1[C:18](=[O:25])[O:19][C:20]2=[O:24])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[CH2:9]([N:16]1[C@H:17]([C:18](=[O:25])[NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:23][CH2:22][C@@H:21]1[C:20]([OH:19])=[O:24])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 222355968-Benzyl-3-oxa-8-azabicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 69622412cis-1-Benzyl-5-(N-benzylcarbamoyl)-pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylamine (25.7 g, 0.24 mol) was added to an ice cold solution of 8-benzyl-3-oxa-8-azabicyclo[3.2.1]octan-2,4-dione (0.24 mol; from step (a) above) in CH2Cl2 (1 L). The solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in Et2O and extracted with 2 N NaOH solution. The aqueous base layer was separated and acidified to pH 4. The precipitated product was collected and dried to afford 49.5 g (61% for two steps) of the sub-title compound as a tan solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in Et2O
  3. extractionextracted with 2 N NaOH solution
  4. customThe aqueous base layer was separated
  5. customThe precipitated product was collected
  6. customdried

Sources & evidence

ORD record
ord-8172ff70c7484a7db438f7c589a65a54
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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