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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2373521Generated: October 28, 2026

Triethylamine → HCID 72444859, compound

https://huagongshe.com/reaction/2373521

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantDimethyl acetylenedicarboxylateHCID 12980—
ReactantHydroxyamine hydrochlorideHCID 443297—
ReactantPhenylmethyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylateHCID 21112384—
SolventMethanolHCID 887—
ProductHCID 72444859HCID 72444859—

Reaction Steps

Triethyl amine (1.5 eq.), hydroxylamine hydrochloride (1.3 eq.) were added to a solution of benzyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylate (C-37) in absolute methanol. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was dissolved in chloroform and treated with dimethylacetylene dicarboxylate (2 eq.) for 14 hours at 60° C. The reaction mixture was then concentrated and the resulting crude oil was purified by flash chromatography (petroleum ether/EtOAc 1:1) to give the titled compound (C-38) as a mixture of isomers.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07459452B2
Source datasetuspto-grants-2008_12
ORD IDord-8c1ebf4a366c41d8ae5a193a5d2d36d8
Source noteuspto-grants-2008_12