Ammonium formate → tert-Butyl 4-(1H-indol-3-yl)piperidine-1-carboxylate

HRID 58663Notes

Reaction equation

HRID 58663 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH:7]1[C:8]2[C:4](=[CH:3][CH:2]=[CH:10][CH:9]=2)[C:5]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:6]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12072032tert-butyl 4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 22405349tert-Butyl 4-(1H-indol-3-yl)piperidine-1-carboxylateYield 65.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C 10% (0.25 g) was added to the suspension of tert-butyl 4-(5-chloro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.10 g; 3.31 mmol) in a mixture of methanol (100 mL) and ammonium formate (2.71 g; 42.97 mmol). The mixture was refluxed for 20 hours and was filtered through celite. The filtrate was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent: 0 to 10% ethyl acetate in dichloromethane) to give 0.65 g (61%) of the title compound as a pink solid.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe crude material was purified by flash chromatography on silica gel (eluent: 0 to 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-3920c467acf34b42bb773c64069e61db
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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