Triethylamine → 2-[(3SR,4RS)-3-[(RS)-1-(5-Chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-hexahydro-pyrrolo[1,2-a]pyrazin-6-one

HRID 1158665Notes

Reaction equation

HRID 1158665 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([CH:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:14][N:13]([C:24](Cl)=[O:25])[CH2:12]2)[CH3:10])=[N:6][CH:7]=1.CCN(CC)CC.[CH2:34]1[NH:39][CH2:38][CH2:37][N:36]2[C:40](=[O:43])[CH2:41][CH2:42][CH:35]12>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]([CH:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:14][N:13]([C:24]([N:39]3[CH2:38][CH2:37][N:36]4[C:40](=[O:43])[CH2:41][CH2:42][CH:35]4[CH2:34]3)=[O:25])[CH2:12]2)[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10820612Octahydropyrrolo[1,2-a]piperazin-6-oneHCID 866281803-[(RS)-1-(5-Chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride

Product 1

HCID 673269192-[(3SR,4RS)-3-[(RS)-1-(5-Chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-hexahydro-pyrrolo[1,2-a]pyrazin-6-oneYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3SR,4RS)-3-[(RS)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride (22 mg, 0.051 mmol) in CH2Cl2 (3 mL) were added Et3N (0.015 ml, 0.11 mmol) and hexahydro-pyrrolo[1,2-a]pyrazin-6-one (commercially available) (9 mg, 0.064 mmol). Stirring was continued overnight, and the reaction mixture was concentrated under vacuo and directly purified by flash chromatography (SiO2, EtOAc) to yield 7 mg (25%) the title compound as light yellow oil. ES-MS m/e: 539.2 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuo
  2. customdirectly purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-d2bfad3363b84e5ea81608481a212b79
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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