tert-butyl 4-(4-amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylate → Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

HRID 2272420노트

반응식

HRID 2272420 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:4][C:3]=1[O:21][CH3:22]>CN(C=O)C.CCO.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:21][CH3:22]

참가 물질

5

반응물 1

HCID 68455699tert-butyl 4-(4-amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylate

생성물 1

HCID 57416157Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 10% Pd/C (0.068 g) in DMF (2 mL) under nitrogen was added a solution of tert-butyl 4-(4-amino-3-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I33) (2.0 g, 6.5 mmol) in EtOH (50 mL) and the resulting suspension was stirred under an atmosphere of hydrogen at room temperature for 24 hours. The reaction mixture was filtered through celite, washing with ethyl acetate (100 mL). The filtrate was evaporated to dryness to give the title compound (I26) (1.42 g, 72%) as a light brown solid; 1H NMR (400 MHz, CDCl3) δ 6.66-6.58 (m, 3H), 4.21 (s, 2H), 3.76-3.66 (m, 4H), 2.53 (tt, J=12.1, 3.5 Hz, 1H), 1.84-1.75 (m, 2H), 1.55 (tdd, J=11.5, 6.4, 3.1 Hz, 1H), 1.47 (s, 9H).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashing with ethyl acetate (100 mL)
  3. customThe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-564e4cecf8b94dc181fc0618175b0bf0
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120761B2

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