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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1071503Generated: October 30, 2026

Water → 4-Azido-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

https://huagongshe.com/reaction/1071503

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium AzideHCID 33557—
Reactant4-Methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl EsterHCID 19790396—
ReactantEthyl acetate hexaneHCID 21226206—
SolventDimethylformamideHCID 6228—
Product4-Azido-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl EsterHCID 14041195—

Reaction Conditions

Temperature60 °C

Reaction Steps

The 4-methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (135.21 mg, 0.48 mmol) was taken up in dry DMF under argon and sodium azide (156.00 mg, 2.40 mmol) was added. The reaction was then heated to 60° C. for 48 h. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with sat NaHCO3 and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (5:1 hexane-ethyl acetate) Yield 93.41 mg.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06906067B2
Source datasetuspto-grants-2005_06
ORD IDord-f5b78fb38d1c45b3b62efda05b70320a
Source noteuspto-grants-2005_06