Trifluoroacetic acid → HCID 131732391, compound

HRID 921670Notes

Reaction equation

HRID 921670 reaction equation
[F:1][C@H:2]1[C@@H:7]([NH:8][C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C@H:2]1[C@@H:7]([NH:8][C:9](=[O:10])[O:11][CH3:12])[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708535HCID 86708535, compound

Product 1

HCID 131732391HCID 131732391, compoundYield 140%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R,4S)-tert-butyl 3-fluoro-4-((methoxycarbonyl)amino)piperidine-1-carboxylate (127 mg, 0.460 mmol) was taken up in DCM (5 mL) and TFA (0.708 mL, 9.19 mmol) was added. The reaction was stirred at room temperature for 1 h. The solvent was removed in vacuo and the material was dissolved in MeOH. The solution was loaded onto an SCX column (5 g, benzenesulfonic acid sorbent) and the column was rinsed with MeOH, followed by 7N NH3/MeOH to obtain the product. The solvent was removed in vacuo to obtain methyl ((3R,4S)-3-fluoropiperidin-4-yl)carbamate (113.5 mg) as a colorless gum. The crude material was taken onto the next step without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe material was dissolved in MeOH
  3. washthe column was rinsed with MeOH
  4. customto obtain the product
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-89e62dc5d9c040588ec2753d4f5ce986
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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