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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1069736Generated: October 29, 2026

N-(tert-Butoxycarbonyl)-D-prolinal → tert-butyl (2R)-2-ethynylpyrrolidine-1-carboxylate

https://huagongshe.com/reaction/1069736

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-(tert-Butoxycarbonyl)-D-prolinalHCID 7009153—
ReactantDiazomethyl-phosphonic-acid-diethylesterHCID 10943016—
ReactantPotassium tert-butoxideHCID 23665647—
SolventDiethyl EtherHCID 3283—
Producttert-butyl (2R)-2-ethynylpyrrolidine-1-carboxylateHCID 10262067—

Reaction Steps

(R)-N-Boc-2-Ethynyl-pyrrolidine was prepared according to Method X above by the treatment of (R)-N-Boc-2-formyl-pyrrolidine (700 mg, 3.51 mmol) (Example 89A) with potassium tert-butoxide (510 mg, 4.56 mmol) and diazomethyl-phosphonic-acid-diethylester (820 mg, 4.56 mmol) (also prepared according to Method X). (R)-N-Boc-2-Ethynyl-pyrrolidine was obtained after silica gel coloumn chromatography with 10% Et2O in hexanes. (Yield 150 mg, 25%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06252086B1
Source datasetuspto-grants-2001_06
ORD IDord-a1a41132ee4844dd872c0f90d2646050
Source noteuspto-grants-2001_06