Triethylamine → (5)-1-(4-Methylbenzyl)-2-oxopyrrolidin-3-yl methanesulfonate

HRID 716082Notes

Reaction equation

C(N(CC)CC)C.[OH:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:10]1=[O:22].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:10]1=[O:22])(=[O:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (0.509 ml, 3.65 mmol) was added to a cooled solution of (S)-3-hydroxy-1-(4-methylbenzyl)pyrrolidin-2-one (0.5 g, 2.436 mmol, intermediate I) in anhydrous DCM (12.18 ml) at 0° C. under a nitrogen atmosphere. Methanesulfonyl chloride (0.198 ml, 2.56 mmol) was then added dropwise and the reaction was allowed to stir at 0° C. for 15 min before quenching with a satd. sodium bicarbonate solution (10 mL). The mixture was allowed to warm to rt and the aqueous layer was separated and extracted with DCM (2×). The combined organic layers were dried over MgSO4 and evaporated in vacuo to give a white solid (0.73 g) which was then purified by silica gel chromatography (40 g of silica) eluting with a gradient of 0% to 50% ethyl acetate in hexanes to provide 0.63 g (91%) of the desired product as a white solid.

Workup

custombefore quenching with a satd
temperatureto warm to rt
customthe aqueous layer was separated
extractionextracted with DCM (2×)
dry with materialThe combined organic layers were dried over MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-04c951da14894d5e832840e679eee944
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187506B2

Reaction notes

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