Hydrochloric Acid → 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane

HRID 376002Notes

Reaction equation

[CH2:1]([C@H:8]([N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])[C@@H:9](OS(C)(=O)=O)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl>O1CCCC1.ClCCl.O>[C:2]1([CH2:1][C@@H:8]([C@H:9]2[CH2:10][O:11]2)[N:17]2[C:18](=[O:27])[C:19]3=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]3[C:21]2=[O:22])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

2.16 g of N-[1(S)-benzyl-3-hydroxy-2(R)-(methylsulphonyloxy)propyl]phthalimide were added to a stirred suspension of 200 mg of sodium hydride (80% dispersion in mineral oil) in 50 ml of dry tetrahydrofuran and the mixture was stirred at 20° C. for 2 hours. A further 100 mg of sodium hydride were added and the stirring was continued for 3.5 hours. The mixture was diluted with dichloromethane and water and the pH of the aqueous layer was adjusted to 7 by adding 2M hydrochloric acid. The organic layer was separated, washed with saturated sodium chloride solution and evaporated. The residue was chromatographed on silica gel using ethyl acetate/n-hexane (1:2) for the elution to give 0.67 g of 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane as a white solid, MS: m/e 294 [M+H]+.

Workup

waitthe stirring was continued for 3.5 hours
customThe organic layer was separated
washwashed with saturated sodium chloride solution
customevaporated
customThe residue was chromatographed on silica gel
washfor the elution

Sources & evidence

ORD record: ord-f0bb9285bfbb436e9ec7fbdcf4811f9d
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488115

Reaction notes

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