N-Hydroxyphthalimide → 2-[[(2R)-2-Methyloxiranyl]methoxy]-1H-isoindole-1,3(2H)-dione

HRID 270119Notes

Reaction equation

[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[N+](C1C=C(S(O[CH2:26][C@@:27]2([CH3:30])[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O>>[CH3:26][C@:27]1([CH2:30][O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:29][O:28]1

Participants

Reactant 2

HCID 10665N-Hydroxyphthalimide

HCID 57463982HCID 57463982, compound

Product 1

HCID 866014882-[[(2R)-2-Methyloxiranyl]methoxy]-1H-isoindole-1,3(2H)-dione

Procedure

Prepared from N-hydroxyphthalimide and [(2R)-2-methyloxiran-2-yl]methyl 3-nitrobenzenesulfonate (Chen, J.; Shum, W., Tetrahedron Letters, 1993, 34(48), 7663-6) by the method of Example 93 Step I.

Sources & evidence

ORD record: ord-72103af169b9403cb37864130d9940fb
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449475B2

Reaction notes

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