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

HRID 1593475Notes

Reaction equation

HRID 1593475 reaction equation
[CH2:1]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C@H:8]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:6])[CH:2]=[CH2:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66952501(3S,4R)-1-tert-butyl 3-ethyl 4-(allyloxycarbonyl)piperidine-1,3-dicarboxylate

Product 1

HCID 86609246(3S,4R)-ethyl 4-(allyloxycarbonyl)piperidine-3-carboxylateYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 259B (680 mg, 1.9 mmol) in CH2Cl2 (10 mL) was treated with TFA (1 mL) at room temperature. The reaction mixture was stirred for 16 hours, then concentrated. The residues was dissolved in EtOAc (20 mL) and washed with saturated aqueous NaHCO3 (2×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 170 mg of Compound 259C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residues was dissolved in EtOAc (20 mL)
  3. washwashed with saturated aqueous NaHCO3 (2×20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed44aafa72904d74af1c1a510447dea6
Source dataset
uspto-grants-2007_11
Patent number
US07297695B2

Reaction notes

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