Phthalimide → cis-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600726Notes

Reaction equation

HRID 600726 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([C:11]([CH2:16]O)=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:37]1(=[O:47])[NH:41][C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([C:11]([CH2:16][N:41]3[C:37](=[O:47])[C:38]4[C:39](=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:40]3=[O:42])=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68971833cis-3-Hydroxymethyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Product 1

HCID 68974090cis-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To alcohol 7 (1.13 g; 4.67 mmol), triphenyl phosphine (1.28 g; 4.88 mmol) and phthalimide (0.73 g; 4.96 mmol) in THF (75 mL) was added DIAD (0.98 mL; 4.94 mmol). The reaction mixture was stirred at room temperature overnight. The volatiles were evaporated and the residue chromatographed with 50% ethyl acetate/hexanes to yield phthalimide 8 as a white foam.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue chromatographed with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a813f7a285b948aba051307744a7a90b
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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