Hydrochloric Acid → (3aRS,7aRS)-7,7-dimethyl-4-perhydroisoindolone hydrochloride

HRID 55405Notes

Reaction equation

C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([CH3:19])([CH3:18])[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)C1C=CC=CC=1.[ClH:20]>C(O)C.[OH-].[OH-].[Pd+2]>[ClH:20].[CH3:18][C:11]1([CH3:19])[CH:10]2[CH:15]([CH2:16][NH:8][CH2:9]2)[C:14](=[O:17])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2.31 g of (3aRS,7aRS)-2-benzyl-7,7-dimethyl-4-perhydroisoindolone and 9.96 cm3 of 1N hydrochloric acid in 25 cm3 of anhydrous ethanol is heated to 60° C. with stirring; 0.11 g of 20% palladium hydroxide on charcoal is added and the reaction mixture is then hydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure. After reaction for 6 hours, the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). 2.17 g of (3aRS,7aRS)-7,7-dimethyl-4-perhydroisoindolone hydrochloride are obtained, in the form of a pink oil containing ethanol.

Workup

stirringhydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure
customAfter reaction for 6 hours
filtrationthe reaction mixture is filtered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-c6829b299962429aa5f4ead312dced77
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624950

Reaction notes

Loading…