Oxalyl chloride → 3,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione hydrochloride

HRID 1743700Notes

Reaction equation

HRID 1743700 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH2:7]([N:14]1[C@H:18]([C:19](=[O:28])[NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16][C@@H:15]1[C:29]([OH:31])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[ClH:4].[CH2:21]([N:20]1[C:29](=[O:31])[CH:15]2[N:14]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:18]([CH2:17][CH2:16]2)[C:19]1=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 69622412cis-1-Benzyl-5-(N-benzylcarbamoyl)-pyrrolidine-2-carboxylic acid

Product 1

HCID 222356423,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione hydrochlorideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (18.5 g, 0.14 mol) was added dropwise to an ice cold suspension of cis-1-benzyl-5-(N-benzylcarbamoyl)-pyrrolidine-2-carboxylic acid (49.5 g, 0.14 mol; from step (b) above) in CH2Cl2 (500 mL) at such a rate that the reaction temperature did not exceed 8° C. The reaction slowly warmed to room temperature overnight with stirring. The reaction mixture was then concentrated in vacuo. The residue was slurried with 2-propanol and filtered to afford 39.5 g (84%) of the sub-title compound as a light tan solid.

Workup

  1. customdid not exceed 8° C
  2. customThe reaction
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-cb746dcdea2b44cfa6c41c5f03e985e6
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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