Triethylamine → Methyl (2S,4R)-4-methylsulfonyloxy-1-methyl-2-pyrrolidinecarboxylate

HRID 1797452Notes

Reaction equation

C(N(CC)CC)C.Cl.[OH:9][C@H:10]1[CH2:14][N:13]([CH3:15])[C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1.[S:20](Cl)([CH3:23])(=[O:22])=[O:21].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:23][S:20]([O:9][C@H:10]1[CH2:14][N:13]([CH3:15])[C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1)(=[O:22])=[O:21]

Participants

Conditions

Temperature: 40 °C

Procedure

Triethylamine (1.53 mL) was added to a suspension of methyl (2S,4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylate hydrochloride (1 g) obtained from Reference example 1 or 3 in tetrahydrofuran (10 mL) and the mixture was stirred at 40° C. for 3 hours. Mesyl chloride was added to the mixture under ice cooling and the mixture was stirred for 2 hours. Ethyl acetate (20 mL) and 5% aqueous sodium hydrogencarbonate solution (10 mL) were added to the reaction mixture, which was then extracted. The organic layer was separated from the aqueous layer and the solvent of the organic layer was removed by distillation under reduced pressure to give the title compound (1.0 g, yield 83%).

Workup

stirringthe mixture was stirred for 2 hours
extractionwas then extracted
customThe organic layer was separated from the aqueous layer
customthe solvent of the organic layer was removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-25ef57a0e9b541b8b790fc96b3388687
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034150B2

Reaction notes

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