(R)-(-)-N-(2,3-Epoxypropyl)phthalimide → 2-[(2r)-3-Fluoro-2-hydroxypropyl]-1h-isoindole-1,3-dione
Reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[FH:16].[F-].[K+]>>[F:16][CH2:3][C@H:2]([OH:1])[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]Participants
3
Procedure
A sample of 2-[(2R)-Oxiranylmethyl]-1H-isoindole-1,3-dione (G. Alexander et al. Tetrahedron Asymmetry, 7, 1641–8, 1996) is treated with potassium hydrogen difluoride to give 2-[(2R)-3-fluoro-2-hydroxypropyl]-1H-isoindole-1,3-dione in the presence of catalyst nBu4NH2F3. The procedures and methods used in this synthesis are identical to those of Example 3, except that in step Example-3B 2-[(2R)-3-fluoro-2-hydroxypropyl]-1H-isoindole-1,3-dione is used instead of (S)-1-[(benzyloxycarbonyl)amino]-2-propanol to produce the title product.
Sources & evidence
- ORD record
- ord-88fce86387c9491da308750ea676d854
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196118B2
Reaction notes
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