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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1917295Generated: November 2, 2026

Hydrochloric Acid → (R)-6-Methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl ester

https://huagongshe.com/reaction/1917295

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium HydroxideHCID 14798—
Reactant(R)-6-Methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl ester 1-methyl esterHCID 67491017—
SolventMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
Product(R)-6-Methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl esterHCID 67490768—

Reaction Steps

A 1N sodium hydroxide solution (23 mL) was added dropwise to a mixed solution of (R)-6-methyl-3-azabicyclo[3.2.0]heptane-1,3-dicarboxylic acid 3-benzyl ester 1-methyl ester (3.5 g, 11.5 mmol) in tetrahydrofuran (60 mL) and methanol (20 mL) under ice-cooling, and the mixture was stirred for 30 minutes. The reaction solution was neutralized with 1N hydrochloric acid, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure to give 3.4 g (quantitative) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618094B2
Source datasetuspto-grants-2013_12
ORD IDord-1000235a0d9a420cab8702599ea503ae
Source noteuspto-grants-2013_12