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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 732651Generated: October 26, 2026

Diisopropylethylamine → 4-(methoxycarbonyl)phenyl (3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-pyridin-3-ylpyrrolidine-1-carboxylate

https://huagongshe.com/reaction/732651

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantMethyl 4-[(chlorocarbonyl)oxy]benzoateHCID 854163—
Reactant3-[(3S,4R)-4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyrrolidin-3-yl]pyridineHCID 68912023—
SolventTetrahydrofuranHCID 8028—
Product4-(methoxycarbonyl)phenyl (3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-pyridin-3-ylpyrrolidine-1-carboxylateHCID 86628534—

Reaction Steps

3-[(3S,4R)-4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyrrolidin-3-yl]pyridine and N,N-diisopropylethylamine were dissolved in THF, methyl 4-[(chlorocarbonyl)oxy]benzoate (mfd. by Fluka) was added in one portion thereto at room temperature and stirred for 3 hours, and then the reaction solution was concentrated under a reduced pressure. Work-up and purification of the residue was carried out in the standard method to produce 4-(methoxycarbonyl)phenyl (3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-pyridin-3-ylpyrrolidine-1-carboxylate.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07585886B2
Source datasetuspto-grants-2009_09
ORD IDord-13ddc789536d4551b71306c92cac4b6a
Source noteuspto-grants-2009_09