Dimethylamine → (2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine

HRID 1109811Notes

Reaction equation

HRID 1109811 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][NH:16][CH3:17]>O1CCCC1>[CH3:15][N:16]([CH3:17])[C:9]([C@@H:8]1[CH2:13][C@H:11]([SH:10])[CH2:12][N:7]1[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[O:14]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 15227998(1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one

Product 1

HCID 10083864(2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one (37.3 mg) in tetrahydrofuran (0.3 ml) was added an aqueous 40% dimethylamine solution (39.2 mg). The mixture was stirred for 2 hours at room temperature. After the reaction was over, the same post-treatment as in Example 5-(1) was conducted, thereby to give oily (2S,4S)-N,N-dimethyl-1-allyloxycarbonyl -4-mercapto-2-pirrolidinecarboxamide.

Sources & evidence

ORD record
ord-01225d84a4ec41c7a2d1fca3b3cdf905
Source dataset
uspto-grants-1994_06
Patent number
US05322952

Reaction notes

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