Sodium Chloride → methyl (2S,4S)-4-acetylthio-1-methyl-2-pyrrolidinecarboxylate

HRID 1797453Notes

Reaction equation

[C:1]([O-:4])(=[S:3])[CH3:2].[K+].CS(O[C@H:11]1[CH2:15][N:14]([CH3:16])[C@H:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1)(=O)=O.C(OCC)(=O)C.[Cl-].[Na+]>C(O)C.O>[C:1]([S:3][C@@H:11]1[CH2:15][N:14]([CH3:16])[C@H:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]1)(=[O:4])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium thioacetate (677 mg) was added to a solution of methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylate (609 mg) obtained from Reference example 4 in ethanol/water (9:1) (6 ml), and the resulting mixture was stirred at 80° C. for 3 hours, and then the mixture was allowed to stand overnight at the same temperature. Ethyl acetate (20 mL) and 10% aqueous sodium chloride solution (10 mL) were added to the reaction mixture, which was then extracted. The organic layer was separated from the aqueous layer, which was washed with water (10 mL). The solvent of the organic layer was removed by distillation under reduced pressure to give the title compound (543 mg, yield 97%).

Workup

waitto stand overnight at the same temperature
extractionwas then extracted
customThe organic layer was separated from the aqueous layer, which
washwas washed with water (10 mL)
customThe solvent of the organic layer was removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-09b469cb52ec4d4aa82a44af911615d7
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034150B2

Reaction notes

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