Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-5-(benzyloxy)pyrrolidin-2-one

HRID 1761886Notes

Reaction equation

[CH2:1]([O:8][CH:9]1[NH:13][C:12](=[O:14])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)C>[C:25]1([S:31]([N:13]2[CH:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:10][CH2:11][C:12]2=[O:14])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At ambient temperature and under an inert atmosphere, 4.40 g of 5-benzyloxypyrrolidin-2-one is added to a solution of 4.64 g of sodium bis(trimethylsilyl) amide in 350 cm3 of anhydrous ethyl ether. The mixture is agitated for 30 minutes, then cooled to 0° C., and a solution of 4.06 g of benzenesulphonyl chloride in 30 cm3 of anhydrous ether is added, while maintaining the temperature at 0° C. The temperature is allowed to return to the ambient, then, after filtering and evaporating the solvent under reduced pressure, the residue is chromatographed on silica, eluting with a mixture of ethyl acetate and n-hexane (1-2). After re-crystallizing from a mixture of benzene and n-hexane (1-3), 2.25 g of the expected product is obtained, m.p. 80°-81° C.

Workup

temperaturewhile maintaining the temperature at 0° C
filtrationafter filtering
customevaporating the solvent under reduced pressure
customthe residue is chromatographed on silica
washeluting with a mixture of ethyl acetate and n-hexane (1-2)
customAfter re-crystallizing from a mixture of benzene and n-hexane (1-3)

Sources & evidence

ORD record: ord-762daad8e7854ce6a5774a985f567c66
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04829079

Reaction notes

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