Hydrochloric Acid → Benzyl-cis-4-fluoropiperidin-3-ylcarbamate

HRID 408138Notes

Reaction equation

HRID 408138 reaction equation
Cl.O1CCOCC1.[CH2:8]([O:15][C:16]([NH:18][C@H:19]1[C@@H:24]([F:25])[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([O:15][C:16](=[O:17])[NH:18][C@H:19]1[C@@H:24]([F:25])[CH2:23][CH2:22][NH:21][CH2:20]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131729719cis-Tert-butyl 3-(benzyloxycarbonylamino)-4-fluoropiperidine-1-carboxylate

Product 1

HCID 68085864Benzyl-cis-4-fluoropiperidin-3-ylcarbamateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4N HCl in dioxane (3.29 mL, 13.2 mmol) was added to a solution of cis-tert-butyl 3-(benzyloxycarbonylamino)-4-fluoropiperidine-1-carboxylate (0.58 g, 1.65 mmol) in DCM (3 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo. The resulting solid was dissolved in water (5 mL) and extracted with ether (10 mL). The resulting aqueous layer was basified with 30% potassium carbonate to a pH of about 10 and extracted with DCM (2×30 mL). The combined organic layer was dried (sodium sulfate) and concentrated in vacuo to give benzyl-cis-4-fluoropiperidin-3-ylcarbamate (0.39 g, 94%) as a solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe resulting solid was dissolved in water (5 mL)
  3. extractionextracted with ether (10 mL)
  4. extractionextracted with DCM (2×30 mL)
  5. dry with materialThe combined organic layer was dried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5595f5cae0ef41f096fe855f1ac63176
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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