Hydrochloric Acid → (R)-3-(pyrrolidin-2-ylmethoxy)picolinamide dihydrochloride

HRID 869626Notes

Reaction equation

HRID 869626 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2C(OC(C)(C)C)=O)=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2].C(OC(C)C)(C)C.[ClH:31]>C(OCC)(=O)C>[ClH:31].[ClH:31].[NH:13]1[CH2:14][CH2:15][CH2:16][C@@H:12]1[CH2:11][O:10][C:9]1[C:4]([C:1]([NH2:2])=[O:3])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 66961823(R)-tert-butyl 2-((2-carbamoylpyridin-3-yloxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 66960633(R)-3-(pyrrolidin-2-ylmethoxy)picolinamide dihydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-tert-butyl 2-((2-carbamoylpyridin-3-yloxy)methyl)pyrrolidine-1-carboxylate (3.43 g, 10.7 mmol, EXAMPLE 1 Step 2) in 4.0 M hydrogen chloride in ethyl acetate (100 mL) was stirred at room temperature for 5 h. Diisopropyl ether (150 mL) was added to the mixture, and the formed white precipitate was collected by filtration. The precipitate was dried under reduced pressure to give 2.89 g (92%) of the title compound as a white solid.

Workup

  1. filtrationthe formed white precipitate was collected by filtration
  2. customThe precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-af40c2a53b1a45b486f3e3047ea4ee53
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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