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

HRID 633896Notes

Reaction equation

HRID 633896 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-d17e2412df954aba8005f0b45f0c759e
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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