1-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine → 1-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(2-methylpropyl)-2-pyridinyl)amino]piperidine

HRID 361803Notes

Reaction equation

HRID 361803 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 107363161-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine

Product 1

HCID 105216251-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(2-methylpropyl)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]-piperidine (XXV, EXAMPLE 27, 1.07 g, 3.1 mmol) is hydrogenated at 20 psi over night using palladium on carbon (10%, 0.1 g) as catalyst. The reaction is filtered, the solvent evaporated and the concentrate is used without further purification, NMR (300 MHz, CDCl3) 0.66, 1.25, 1.34-1.42, 1.50-1.56, 1.72-1.81, 2.28, 2.46, 2.50-2.56, 3.50-3.13, 3.88, 6.70, 7.21 and 7.98.

Workup

  1. filtrationThe reaction is filtered
  2. customthe solvent evaporated
  3. customthe concentrate is used without further purification, NMR (300 MHz, CDCl3) 0.66, 1.25, 1.34-1.42, 1.50-1.56, 1.72-1.81, 2.28, 2.46, 2.50-2.56, 3.50-3.13, 3.88, 6.70, 7.21 and 7.98

Sources & evidence

ORD record
ord-9d4466ce3b8447e0afcf434871fff4d8
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

Loading…