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

HRID 1593470Notes

Reaction equation

HRID 1593470 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-515acd33ea0f49c688e0e1473be094d5
Source dataset
uspto-grants-2007_11
Patent number
US07297695B2

Reaction notes

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