Hydrochloric Acid → 3-pyrrolidin-3-yloxypyridine:hydrochloride

HRID 82940Notes

Reaction equation

HRID 82940 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH:8]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)[CH:2]=1.[ClH:20]>ClCCl.O1CCOCC1>[ClH:20].[NH:10]1[CH2:11][CH2:12][CH:8]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10801570tert-Butyl 3-(pyridin-3-yloxy)pyrrolidine-1-carboxylate

Product 1

HCID 534092893-pyrrolidin-3-yloxypyridine:hydrochlorideYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a cooled solution of tert-butyl 3-(pyridin-3-yloxy)pyrrolidine-1-carboxylate (600 mg, 2.27 mmol; which may be prepared as described in Step 1) in dichloromethane (15 mL) was added dropwise HCl 4N in dioxane (11.1 mL). The solution was warmed to room temperature and stirred for 1 h. The solvent was evaporated under reduced pressure to give the title compound (263 mg, 58%) as a yellow wax.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e01fe83dae154b26a679d904e99d3f51
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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