N-hydroxy-2-pyridinecarboximidoyl chloride → cis-3-(Pyridin-2-yl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600722Notes

Reaction equation

HRID 600722 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([C:11]([C:16]3C=N[C:19](OC)=[CH:20][CH:21]=3)=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:25]=[C:26](Cl)C1C=CC=CN=1>CO.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:26][N:25]=3)=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 421736N-hydroxy-2-pyridinecarboximidoyl chlorideHCID 68971835cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Product 1

HCID 68971960cis-3-(Pyridin-2-yl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in an analogous manner as the 4-methoxy-3-pyridyl cycloadduct 3c using chloro oxime 2e. 3e was isolated as a white solid after chromatography with 1.5% methanol/methylene chloride.

Sources & evidence

ORD record
ord-5b22c20621974550bb808c0148f777e7
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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