Hydrochloric Acid → (R)-2-chloro-5-fluoro-3-(pyrrolidin-2-yl)pyridine dihydrochloride

HRID 1426919Notes

Reaction equation

HRID 1426919 reaction equation
[Cl:1][C:2]1[C:7]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2C(OC(C)(C)C)=O)=[CH:6][C:5]([F:20])=[CH:4][N:3]=1.[ClH:21]>O1CCOCC1>[ClH:1].[ClH:21].[Cl:1][C:2]1[C:7]([C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:6][C:5]([F:20])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86664582(R)-tert-butyl 2-(2-chloro-5-fluoropyridin-3-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86664583(R)-2-chloro-5-fluoro-3-(pyrrolidin-2-yl)pyridine dihydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a dioxane (5 mL) solution of (R)-tert-butyl 2-(2-chloro-5-fluoropyridin-3-yl)pyrrolidine-1-carboxylate (500 mg, 1.66 mmol) was added HCl (4 N dioxane, 20 mL), followed by stirring at ambient temperature overnight. The mixture was concentrated and treated with Et2O, then vacuum-dried, to provide the product as a white solid (0.36 g, 80% yield). MS (apci) m/z=201.1 (M+H). The enantiomeric excess (ee %) of the product was determined to be >92% according to the method described in Preparation A.

Workup

  1. concentrationThe mixture was concentrated
  2. additiontreated with Et2O
  3. customvacuum-dried

Sources & evidence

ORD record
ord-a8fd0e66458942e3b1b77980249186a4
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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