Trifluoroacetic acid → Isopropyl 4-aminopiperidine-1-carboxylate

HRID 448584

Reaction equation

HRID 448584 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([NH:13]C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([NH2:13])[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597771674-Tert-butoxycarbonylamino-piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 46941577Isopropyl 4-aminopiperidine-1-carboxylateYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 18a (3.26 g, 11.37 mmol) in 10 mL of DCM, was added TFA (5 mL, 64.9 mmol). The mixture was stirred at room temperature for 2 h and the solvent were evaporated. The residue was dissolved in DCM and a saturated solution of NaHCO3 and 1N NaOH were added until pH was 8. The layers were separated and the aqueous layer was extracted with 3:1 DCM:IPA (3×40 mL). The organic extracts were combined, dried, filtered and evaporated to afford 1.89 g (89%) of 18b.

Workup

  1. customthe solvent were evaporated
  2. dissolutionThe residue was dissolved in DCM
  3. additiona saturated solution of NaHCO3 and 1N NaOH were added until pH was 8
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with 3:1 DCM
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-99d07a368f414150bfa89fa12d747a27
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Linked notes

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