cis-Octahydroisoindole hydrochloride

cis-Octahydroisoindole hydrochloride - Names and Identifiers

Name	(3aR,7aS)-octahydro-1H-isoindole hydrochloride (1:1)
Synonyms	Cis-hexahydroisoindolineHCL cis-Octahydro-isoindole Hcl Cis-hexahydroisoindole hydrochloride cis-Octahydroisoindole hydrochloride CIS-HEXAHYDROISOINDOLINE HYDROGEN CHLORIDE Cis-hexahydroisoindoline hydrogen chloride (3aR,7aS)-octahydro-1H-isoindole hydrochloride (3aR,7aS)-rel-Octahydro-1H-isoindole hydrochloride (3aR,7aS)-rel-Octahydro-1H-isoindole hydrochloride 1H-Isoindole,octahydro-, hydrochloride, (3aR,7aS)-rel- (9CI) 5-[2-(4-{[(1S)-4-ethoxy-1-(ethoxycarbonyl)-4-oxobutyl]carbamoyl}phenyl)ethyl]-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-2-aminium
CAS	161829-92-1
EINECS	1806241-263-5
InChI	InChI=1/C8H15N.ClH/c1-2-4-8-6-9-5-7(8)3-1;/h7-9H,1-6H2;1H/t7-,8+

cis-Octahydroisoindole hydrochloride - Physico-chemical Properties

Molecular Formula	C8H16ClN
Molar Mass	161.67234
Melting Point	121-123 °C
Appearance	White solid
Storage Condition	Sealed in dry,Room Temperature

cis-Octahydroisoindole hydrochloride - Reference Information

Description

cis-perhydroisoindole (I) is a key intermediate in the synthesis of mitglinide, therefore, its synthesis has received extensive attention. Miglinide was developed by Kissei Pharmaceutical Company in Japan and was first listed in Japan in 2004 as a new oral hypoglycemic drug for the treatment of type 2 diabetes.

Synthesis method

(3AR,7AS)-REL-octahydro-1H-isoindole hydrochloride Synthesis of dihydroisoindole, and then catalytic hydrogenation to reduce the benzene ring. When the author repeated the literature method, he found that the preparation of dihydroisoindole had the disadvantages of rare raw materials, harsh conditions and low yield. For this reason, directly using phthalimide as a raw material to react with KOH to prepare its potassium salt, and then react with benzyl bromide to obtain N-benzyl phthalimide, and use tetrahydroaluminum lithium to reduce the carbonyl group in the compound N-benzyl phthalimide to obtain N-benzyl dihydroisindole, and then deprotected under Pd/C catalytic hydrogenation to obtain dihydroisindole, and finally reduce the benzene ring to obtain (3AR,7AS)-REL-octahydro-1H-isoindole hydrochloride. The method used is easy to obtain raw materials, mild reaction conditions, simple operation and high yield. Or use cis-hexahydrophthalic anhydride as a raw material and react with urea to obtain cis-hexahydrophthalimide, which is then reduced by lithium aluminum hydride and steam distillation to obtain the target product (3AR,7AS)-REL-octahydro-1H-isoindole hydrochloride. The yields of the two-step reaction were 71.9% and 78.3% respectively. This method is easy to operate and easy for industrial production. (3AR,7AS)-REL-octahydro-1H-isoindole hydrochloride synthesis reaction formula is as follows:

Last Update：2024-04-10 22:29:15