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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 417484Generated: October 28, 2026

Trimethylsilyldiazomethane → 4-(2-Diazo-acetyl)-piperidine-1-carboxylic acid benzyl ester

https://huagongshe.com/reaction/417484

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethylsilyldiazomethaneHCID 167693—
ReactantBenzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 2776270—
SolventDichloromethaneHCID 6344—
Product4-(2-Diazo-acetyl)-piperidine-1-carboxylic acid benzyl esterHCID 86648882102.1%

Reaction Steps

4-Chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (43 g, 0.15 mol) in dichloromethane (300 mL) was treated with (trimethylsilyl)diazomethane (2.0 M in hexanes, 150 mL, 0.31 mol) over 15 min. The reaction mixture was stirred at ambient temperature for 18 hours and the mixture was concentrated to afford crude 4-(2-diazo-acetyl)-piperidine-1-carboxylic acid benzyl ester (44 g), which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08088368B2
Source datasetuspto-grants-2012_01
ORD IDord-17766aa580904d308bf3aec3baf00940
Source noteuspto-grants-2012_01