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

HRID 613377Notes

Reaction equation

HRID 613377 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-amino)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, 1 H), 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-160bc77a9a024c4f9d545bb82e772016
Source dataset
uspto-grants-1999_12
Patent number
US06008213

Reaction notes

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