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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 617339Generated: October 30, 2026

Triphenylphosphine → 3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-5-trifluoromethylpyridine

https://huagongshe.com/reaction/617339

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
ReactantN-(tert-Butoxycarbonyl)-D-prolinolHCID 688279—
ReactantDiethyl azodicarboxylateHCID 5462977—
Reactant5-(Trifluoromethyl)pyridin-3-olHCID 22989707—
SolventTetrahydrofuranHCID 8028—
Product3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-5-trifluoromethylpyridineHCID 21309660—

Reaction Steps

A 332.9. mg (1.56 mmol) sample of (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol and 224.9 mg (1.30 mmol) of 3-hydroxy-5-trifluoromethylpyridine were reacted with triphenylphosphine and DEAD (1.56 mmol each) in 5 mL of THF according to the procedure of Example 14a, to give 386 mg of the title compound. MS (DCI/NH3) m/e 347 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.50 (s, 1H), 8.48 (s, 1H), 7.46 (s, 1H), 4.28-3.90 (m, 3H), 3.48-3.84 (m, 2H), 2.12-1.87 (m, 4H), 1.47 (s, 9H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05948793
Source datasetuspto-grants-1999_09
ORD IDord-63765be499bb4283bb25dc2c8aa4c6fe
Source noteuspto-grants-1999_09