1-Methylpiperazine → 1-[(2S,4S)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarbonyl]-4-methylpiperazine

HRID 1109813Notes

Reaction equation

HRID 1109813 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][C@@H:11]2[CH2:13][C@H:8]1[C:9](=[O:14])[S:10]2)=[O:6])[CH:2]=[CH2:3].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][C@@H:11]([SH:10])[CH2:13][C@H:8]1[C:9]([N:19]1[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]1)=[O:14])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 15227998(1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one

Product 1

HCID 570725221-[(2S,4S)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarbonyl]-4-methylpiperazine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one (30.6 mg) in tetrahydrofuran (1 ml) was added 4-methylpiperazine (15.8 mg). The mixture was stirred for 33 hours at room temperature. After the reaction was over, the mixture was diluted with ethyl acetate (2 ml). Distillation of the solvent gave oily 1-[(2S,4S)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarbonyl]-4-methylpiperazine.

Workup

  1. distillationDistillation of the solvent

Sources & evidence

ORD record
ord-8405c1e9ae9b46e7a2e902ae461d0054
Source dataset
uspto-grants-1994_06
Patent number
US05322952

Reaction notes

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