Triethylamine → Methyl (R)-1-(3-nitrobenzenesulfonyl)pyrrolidine-2-carboxylate

HRID 1528202Notes

Reaction equation

C(N(CC)CC)C.[N+:8]([C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].Cl.[NH:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[C:27]([O:29][CH3:30])=[O:28]>ClCCl>[N+:8]([C:11]1[CH:12]=[C:13]([S:17]([N:22]2[CH2:26][CH2:25][CH2:24][C@@H:23]2[C:27]([O:29][CH3:30])=[O:28])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

3.38 ml of triethylamine were added dropwise, over the course of 30 minutes, to a solution of 2.56 g of 3-nitrobenzenesulfonyl chloride and 1.91 g of methyl (R)-pyrrolidine-2-carboxylate hydrochloride in 30 ml of dichloromethane (30 ml) cooled to 0° C. The reaction medium was left at ambient temperature and stirred for 1 hour. The reaction medium was diluted with 50 ml of dichloromethane, and washed with a 1 M sodium hydrogen phosphate solution (2×50 ml) and a saturated sodium hydrogen carbonate solution (50 ml). The organic phase was dried over magnesium sulfate and evaporated 3.00 g of methyl (R)-1-(3-nitrobenzenesulfonyl)pyrrolidine-2-carboxylate were obtained and used in the next step without purification.

Workup

waitThe reaction medium was left at ambient temperature
washwashed with a 1 M sodium hydrogen phosphate solution (2×50 ml)
dry with materialThe organic phase was dried over magnesium sulfate
customevaporated 3.00 g of methyl (R)-1-(3-nitrobenzenesulfonyl)pyrrolidine-2-carboxylate
customwere obtained
customused in the next step without purification

Sources & evidence

ORD record: ord-3f1654641e3940428f124d1dd8d645d9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090596B2

Reaction notes

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