4-Methoxy-N-hydroxybenzenecarboximidoyl chloride → cis-3-(4-Methoxyphenyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600719Notes

Reaction equation

HRID 600719 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:21]=[CH:20][C:19](Cl)=[CH:18][CH:17]=3)=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][O:24]C1C=CC(C(Cl)=NO)=CC=1>C(N(CC)CC)C>[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][C:19]([O:24][CH3:23])=[CH:18][CH:17]=3)=[N:12][O:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27633714-Methoxy-N-hydroxybenzenecarboximidoyl chlorideHCID 68971118cis-3-(4-Chlorophenyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Product 1

HCID 68797285cis-3-(4-Methoxyphenyl)-3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound was prepared in an analogous manner as the 4-chlorophenyl cycloadduct 3a using chloro oxime 2b. However, two additional portions of chloro oxime and triethyl amine were used. 3b was isolated as a white solid.

Sources & evidence

ORD record
ord-fd258371b26f405685d0cbb008e9daf2
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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