Cyclohexene → tert-butyl N-[2-(pyridin-2-ylamino)ethyl]carbamate

HRID 1108889Notes

Reaction equation

HRID 1108889 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=1[O-])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1CCCCC=1>CCO.[Pd]>[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 178453672HCID 178453672, compound

Product 1

HCID 18419519tert-butyl N-[2-(pyridin-2-ylamino)ethyl]carbamateYield 200%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (106.4 mg, 0.10 mmole) was added to a solution of 2-[[2-(Boc-amino)ethyl]amino]pyridine-N-oxide (126.7 mg, 0.5 mmole) and cyclohexene (0.25 mL, 0.25 mmole) in absolute EtOH (5 mL), and the mixture was heated to reflux. After 16 hr, the reaction was filtered through celite® and the filtrate was concentrated. The residue was combined with the residue obtained from a separate preparation (0.5 mmole scale), and the combined materials were purified by silica gel chromatography (5% MeOH/CHCl3). The title compound (148.4 mg, 63% based on 1 mmole of 2-[[2-(Boc-amnino)ethyl]amino]pyridine-N-oxide) was obtained as a yellow oil: TLC (5% MeOH/CHCl3) Rf 0.43; 1H NMR (400, CDCl3) δ 8.05-8.12 (m, 1 H), 7.37-7.46 (m, 1H), 6.53-6.61 (m, 1 H), 6.41 (d, J=8.3 Hz, 1 H), 5.12 (br s, 1 H), 4.86 (br s, 1 H), 3.26-3.51 (m, 4 H), 1.44 (s, 9 H); MS (ES) m/e 238 (M+H)+.

Workup

  1. temperaturethe mixture was heated to reflux
  2. filtrationthe reaction was filtered through celite®
  3. concentrationthe filtrate was concentrated
  4. customobtained from a separate preparation (0.5 mmole scale)
  5. customthe combined materials were purified by silica gel chromatography (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-bb591e82c526416d811a2745ca06cc68
Source dataset
uspto-grants-2000_05
Patent number
US06069158

Reaction notes

Loading…