cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester → cis-3-(6-Trifluoromethylpyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600721Notes

Reaction equation

HRID 600721 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([C:11]([C:16]3[CH:17]=[N:18][C:19](OC)=[CH:20][CH:21]=3)=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON=C(Cl)C1C=NC([C:33]([F:36])([F:35])[F:34])=CC=1>>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[C@H:10]([C:11]([C:16]3[CH:17]=[N:18][C:19]([C:33]([F:36])([F:35])[F:34])=[CH:20][CH:21]=3)=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 68971835cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl esterHCID 76564437N-Hydroxy-6-trifluoromethyl-3-pyridinecarboximidoyl chloride

Product 1

HCID 68974391cis-3-(6-Trifluoromethylpyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Procedure

The title compound was prepared in an analogous manner as the 4-methoxy-3-pyridyl cycloadduct 3c using chloro oxime 2d. 3d was isolated as a white solid after chromatography with 25% ethyl acetate/hexanes.

Sources & evidence

ORD record
ord-747787daef3740548e7e9bd3b17eeae3
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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