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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 83575Generated: October 26, 2026

N-[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamide → 5-(Tert-butyldimethylsilanyloxymethyl)-3-(2,4-dimethoxybenzyl)-3-azabicyclo[3.1.0]hexan-2-one

https://huagongshe.com/reaction/83575

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-[2-(tert-Butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamideHCID 123927604—
CatalystAcetic acid, rhodium(2+) saltHCID 21674—
Solvent(Trifluoromethyl)benzeneHCID 7368—
Product5-(Tert-butyldimethylsilanyloxymethyl)-3-(2,4-dimethoxybenzyl)-3-azabicyclo[3.1.0]hexan-2-oneHCID 8946586435.4%

Reaction Conditions

Temperature50 °C

Reaction Steps

Under argon atmosphere, to a solution of N-[2-(tert-butyldimethylsilanyloxymethyl)allyl]-2-diazo-N-(2,4-dimethoxybenzyl)acetamide (43 mg) in benzotrifluoride (0.4 ml) was added rhodium (II) acetate dimer dihydrate (2.4 mg) at room temperature, and the mixture was stirred at 50° C. for 24 hours. This reaction mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (14.2 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846746B2
Source datasetuspto-grants-2014_09
ORD IDord-b73ca5ad23e647a18625f7baa899dd65
Source noteuspto-grants-2014_09