Trifluoroacetic acid → (3R,4R)-ethyl 4-(benzyloxycarbonyl)piperidine-3-carboxylate

HRID 2261052Notes

Reaction equation

HRID 2261052 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C@@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][NH:14][CH2:13][C@@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66952821(3R,4R)-1-tert-butyl 3-ethyl 4-(benzyloxycarbonyl)piperidine-1,3-dicarboxylate

Product 1

HCID 86609245(3R,4R)-ethyl 4-(benzyloxycarbonyl)piperidine-3-carboxylateYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 254A (243 mg, 0.60 mmol) in CH2Cl2 (3 mL) at 0° C. was treated with trifluoroacetic acid (0.3 mL). The reaction was stirred at room temperature for one hour, then concentrated to an oil. The crude amine was dissolved in EtOAc (10 mL), washed with saturated aqueous NaHCO3 and dried (Na2SO4), filtered and concentrated in vacuo. The product was purified by flash chromatography (10% MeOH/CH2Cl2) on silica gel to afford 95 mg (yield: 52%) of Compound 254B.

Workup

  1. concentrationconcentrated to an oil
  2. dissolutionThe crude amine was dissolved in EtOAc (10 mL)
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (10% MeOH/CH2Cl2) on silica gel

Sources & evidence

ORD record
ord-8603a3d282404a7d906e4283c03480ec
Source dataset
uspto-grants-2010_12
Patent number
US07846931B2

Reaction notes

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