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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1919148Generated: October 26, 2026

Sodium Methoxide → 3,4,6,7,8,9-Hexahydro-6,9-methanopyrazino[1,2-a]indol-1(2H)-one

https://huagongshe.com/reaction/1919148

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium MethoxideHCID 10942334—
ReactantEthyl 3-(2-Aminoethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylateHCID 58044168—
SolventEthanolHCID 702—
Product3,4,6,7,8,9-Hexahydro-6,9-methanopyrazino[1,2-a]indol-1(2H)-oneHCID 5804381654.9%

Reaction Conditions

Temperature65 °C

Reaction Steps

To a solution of ethyl 3-(2-aminoethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylate (334e) (1.8 g, 7.2 mmol) in ethanol (40 mL) was added sodium meth-oxide (2.5 g, 36 mmol). The mixture was heated at 65° C. for 12 hours. It was then cooled to room temperature. The solvent was evaporated to dryness. The residue was purified by column chromatography eluting with 20:1 methylene chloride/methanol to give 334f as a brown solid (800 mg, 53%). MS: [M+H]+ 203.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618107B2
Source datasetuspto-grants-2013_12
ORD IDord-aab68f628d3b48509f91509dddaddb95
Source noteuspto-grants-2013_12