n-Butyl lithium → HCID 3087422, compound

HRID 1193507Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([O:7][CH:8]([CH3:10])[CH3:9])[NH:3]1.[Li+].CCC[CH2-].[CH:16]([S:24](Cl)(=[O:26])=[O:25])=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.CCCCCC>[CH:16]([S:24]([N:3]1[CH:4]([O:7][CH:8]([CH3:10])[CH3:9])[CH2:5][CH2:6][C:2]1=[O:1])(=[O:26])=[O:25])=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: -45 °C

Procedure

To a solution of 3.53 g of 2-oxo-5-isopropyloxy pyrrolidine in 85 cm3 of anhydrous tetrahydrofuran, cooled to -10° C., 15.42 g of a 1.6M solution of N-butyllithium in hexane is added, operating at -10° to -5° C. This is agitated for 30 minutes, while cooling to -45° C., then a solution of 5 g of styrenesulphonyl chloride (CA 47, 3262c, 1953) in 35 cm3 of anhydrous tetrahydrofuran is added slowly, while operating at -45° to -40° C. After allowing a return to ambient temperature, the solvent is evaporated off under reduced pressure and the residue is chromatographed on silica, eluting with a mixture of ethyl ethyl acetate and hexane (1--1). The product obtained is crystallized from ethanol, and 3.1 g of the expected product is obtained. m.p. 92°-94° C.

Workup

customoperating at -10° to -5° C
customwhile operating at -45° to -40° C
customto ambient temperature
customthe solvent is evaporated off under reduced pressure
customthe residue is chromatographed on silica
washeluting with a mixture of ethyl ethyl acetate and hexane (1--1)
customThe product obtained
customis crystallized from ethanol

Sources & evidence

ORD record: ord-50b9389583f94cfcbaa0114a854964e3
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04810722

Reaction notes

Loading…