Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 412576Generated: October 29, 2026

Acetic Acid → 7-[1-(3-Methoxycarbonylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/412576

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantSodium CyanideHCID 8929—
Reactant7-[1-(3-Formylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl esterHCID 11201796—
CatalystHCID 178418406HCID 178418406—
SolventMethanolHCID 887—
SolventChloroformHCID 6212—
Product7-[1-(3-Methoxycarbonylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl esterHCID 11202475—

Reaction Steps

To a soution of 7-[1-(3-formylpyridin-4-yl)piperidin4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (50 mg) in a mixture of chloroform (0.5 ml) and methanol (0.2 ml) were added sodium cyanide (8 mg), manganese dioxide (250 mg) and acetic acid (0.003 ml), and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was filtrated and the solvent was evaporated. The obtained residue was purified by preparative thin layer chromatography (chloroform:methanol=15:1) and dried under reduced pressure to give the title compound (50 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06562828B1
Source datasetuspto-grants-2003_05
ORD IDord-bb5dcad631774167b7b592a920ea4bb6
Source noteuspto-grants-2003_05