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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 36598Generated: October 29, 2026

Diethyl Ether → 4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester

https://huagongshe.com/reaction/36598

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantDi-tert-butyl 4-hydroxypyrazolidine-1,2-dicarboxylateHCID 10334299—
SolventDimethylformamideHCID 6228—
Product4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl esterHCID 54416922—

Reaction Steps

At 0°-5° C., 1.2 g of a sodium hydride dispersion (80 %) are added in portions to a solution of 8.6 g of 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in 90 ml of N,N-dimethylformamide. After stiffing for 30 minutes at 0°-5° C., a solution of 2.5 ml of methyl iodide in 10 ml of N,N-dimethylformamide is added dropwise thereto. Stirring is then continued for 3 hours at 0°-5° C. and then 500 ml of diethyl ether are added thereto. The organic phase is washed with water, dried over sodium sulfate and concentrated to yield 8.0 g of the desired product, 4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tertbutyl ester, in the form of a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05416065
Source datasetuspto-grants-1995_05
ORD IDord-a95fe5a451304b06873d2b8e80483925
Source noteuspto-grants-1995_05