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

HRID 613377노트

반응식

HRID 613377 반응식
[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]

참가 물질

5

반응물 2

HCID 8079CyclohexeneHCID 178453672HCID 178453672, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-160bc77a9a024c4f9d545bb82e772016
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008213

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