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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 712719Generated: October 27, 2026

Triphenylphosphine → HCID 117667237, compound

https://huagongshe.com/reaction/712719

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
Reactant3-Bromo-5-hydroxypyridineHCID 599529—
Reactanttert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 1514399—
ReactantDiisopropyl azodicarboxylateHCID 5363146—
SolventTetrahydrofuranHCID 8028—
ProductHCID 117667237HCID 11766723766.7%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a cooled (0° C.) solution of PPh3 (1.2 g, 4.5 mmol) in THF (50 mL) is added DIAD (0.81 mL, 4.1 mmol), dropwise. After stirring at 0° C. for 15 min, 5-bromo-pyridin-3-ol (441 mg, 2.5 mmol) and (S)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.5 mmol) are added and the mixture is warmed and stirred at room temperature for 16 h. The mixture is concentrated and purified by flash column chromatography to give 596 mg of (R)-3-(5-bromo-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09181272B2
Source datasetuspto-grants-2015_11
ORD IDord-ca57909b744d4f82945c95547dc5f47c
Source noteuspto-grants-2015_11