Ammonium Hydroxide → rac-(3aR,7aR)-octahydro-1H-isoindol-1-one

HRID 1279531Notes

Reaction equation

[C@@H:1]12[C:10](=[O:11])O[C:7](=O)[C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[OH-].[NH4+:13]>>[C:10]1(=[O:11])[C@H:1]2[C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:7][NH:13]1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 12261141(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Product 1

HCID 13039544rac-(3aR,7aR)-octahydro-1H-isoindol-1-oneYield 80%

Procedure

A solution of trans-1,2-cyclohexanedicarboxylic anhydride (10 g, 65 mmol) in ammonium hydroxide (conc., 30 mL) was hydrogenated by the method of EXAMPLE 168 to yield 7.4 g (80%) of the title material.

Sources & evidence

ORD record: ord-68ca077c41184fc58447580054d574c9
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448286B1

Reaction notes

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