tert-Butyl 2-oxo-1'-(2,2,2-trifluoroethyl)-spiro[indoline-3,4'-piperidine]-1-acetate → 2-Oxo-1'-(2,2,2-trifluoroethyl)-spiro[indoline-3,4'-piperidine]-1-acetic acid

HRID 1921184Notes

Reaction equation

HRID 1921184 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:15][CH2:14][N:13]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:21][C:22]([O:24]C(C)(C)C)=[O:23]>C(Cl)Cl.C(C(O)=O)(F)(F)F>[O:1]=[C:2]1[C:10]2([CH2:11][CH2:12][N:13]([CH2:16][C:17]([F:20])([F:18])[F:19])[CH2:14][CH2:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:21][C:22]([OH:24])=[O:23]

Participants

4

Reactant 1

HCID 18449412tert-Butyl 2-oxo-1'-(2,2,2-trifluoroethyl)-spiro[indoline-3,4'-piperidine]-1-acetate

Product 1

HCID 184493632-Oxo-1'-(2,2,2-trifluoroethyl)-spiro[indoline-3,4'-piperidine]-1-acetic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of the tert-butyl 2-oxo-1′-(2,2,2-trifluoroethyl)-spiro[indoline-3,4′-piperidine]-1-acetate from Step B (3.19 g, 8.01 mmol) in CH2Cl2 (16 mL) and CF3CO2H (5 mL) was stirred at ambient temperature for 17 h. Added CF3CO2H (1 mL) and stirred 1 additional hour. The mixture was concentrated in vacuo. To the resulting solid was added an HCl solution (10 mL, 2.0 M in Et2O) and the solution concentrated in vacuo. Repeated two more times to produce the hydrochloride salt of the title compound as a white solid. MS: m/z=343 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the resulting solid was added an HCl solution (10 mL, 2.0 M in Et2O)
  3. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-60e6902b239e4f6c9812d18c052f6df6
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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