4-Methylmorpholine → 2-(1-Pyrrolidinyl)carbonyl-1-benzylpyrrolidine

HRID 369882Notes

Reaction equation

HRID 369882 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:17]1[CH2:22][CH2:21]O[CH2:19][CH2:18]1.ClC(OCC(C)C)=O.N1CCCC1>ClCCl>[N:17]1([C:10]([CH:9]2[CH2:13][CH2:14][CH2:15][N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:12])[CH2:22][CH2:21][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 62365Isobutyl chloroformateHCID 728719N-Benzyl-L-proline

Product 1

HCID 232826462-(1-Pyrrolidinyl)carbonyl-1-benzylpyrrolidineYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzyl-L-proline (50 g) in dichloromethane (300 ml) is cooled with ice. To the solution is added N-methylmorpholine (22.5 g), and then further thereto is added dropwise isobutyl chloroformate (30 g). The mixture is stirred at the same temperature for about one hour, and thereto is added dropwise pyrrolidine (18.8 ml) at the same temperature. The mixture is warmed to room temperature, and stirred for two days. The mixture is washed twice with water (250 ml), and dried over magnesium sulfate. The mixture is concentrated under reduced pressure, and the residue is recrystallized from ethyl acetate-n-hexane to give 2-(1-pyrrolidinyl)carbonyl-1-benzylpyrrolidine (31 g), as white powder.

Workup

  1. stirringstirred for two days
  2. washThe mixture is washed twice with water (250 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customthe residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-520efe8c1c574273821a2b313e60c990
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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