HCID 68762264, compound → Tert-butyl 5-fluoro-2-oxospiro[indoline-3,3'-piperidine]-1'-carboxylate

HRID 529089Notes

Reaction equation

HRID 529089 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH:14]=[CH:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)[C:9](=[O:23])[NH:8][C:5]2=[CH:6][CH:7]=1>C1COCC1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:11]3)[C:9](=[O:23])[NH:8][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68762264HCID 68762264, compound

Product 1

HCID 23500714Tert-butyl 5-fluoro-2-oxospiro[indoline-3,3'-piperidine]-1'-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 5-fluoro-2-oxo-2′,4′-dihydro-1′H-spiro[indoline-3,3′-pyridine]-1′-carboxylate (4.0 g, 13 mmol) in THF (50 mL) was hydrogenated at 50 psi in the presence of 5% Pd/C (1.3 g) overnight. The mixture was filtered. Evaporation of the solvent gave tert-butyl 5-fluoro-2-oxospiro[indoline-3,3′-piperidine]-1′-carboxylate (3.9 g, 97%) as an oil. LCMS (APCI+) m/z 221 [M+H−Boc]+; Rt=3.21 min.

Workup

  1. filtrationThe mixture was filtered
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7acb85e90ac04ebf918826dcffb284de
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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