Hydrochloric Acid → 4-Fluoro-2-azabicyclo[2.1.1]hexane-1-carboxylic acid

HRID 1778481Notes

Reaction equation

HRID 1778481 reaction equation
[F:1][C:2]12[CH2:7][C:5]([C:8]([O:10]C)=[O:9])([CH2:6]1)[N:4](C)[CH2:3]2.Cl>C(Cl)Cl>[F:1][C:2]12[CH2:7][C:5]([C:8]([OH:10])=[O:9])([CH2:6]1)[NH:4][CH2:3]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117697623HCID 117697623, compound

Product 1

HCID 457926464-Fluoro-2-azabicyclo[2.1.1]hexane-1-carboxylic acidYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-fluoro-3-methyl-3-azabicyclo[2.1.1]hexane-4-carboxylate (AR4) (150 mg, 0.57 mmol) in CH2Cl2 (1.0, mL) was added an aqueous of HCl (6.0N, 8.0 mL). The reaction mixture was heated to reflux and stirred for 3 hours. After cooled to room temperature, the solution was filtered. The filtrate was evaporated in vacuo, and the residue was washed with MeCN to give 4-fluoro-2-aza-bicyclo[2.1.1]hexane-1-carboxylic acid as a white solid (45 mg). LC/MS: calc'd 146 (MH+), exp 146 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. filtrationthe solution was filtered
  4. customThe filtrate was evaporated in vacuo
  5. washthe residue was washed with MeCN

Sources & evidence

ORD record
ord-65f5842f5d324545a9f5fbf733a51640
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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