Acetic Acid → Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

HRID 1250695노트

반응식

HRID 1250695 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 176Acetic Acid2회HCID 18326592tert-butyl 4-(2-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 18326585Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 702Ethanol용매

실험 절차

To a solution of 2-[1-tert-butoxycarbonyl-(1,2,3,6-tetrahydropyrdin-4-yl)]benzonitrile (5.3 g, 0.019 mol) and acetic acid (0.28 ml, 4.9 mmol) in ethanol (200 ml), degassed with argon was added palladium on carbon. The reaction was hydrogenated on a Parr capparatus at 50 psi for 15 hours. The mixture was recharged twice with acetic acid (0.14 ml, 0.28 ml) and palladium on carbon (900 mg, 1.8 g), hydrogenated as above and filtered through celite. Solvent evaporation gave 2-(1-tert-butoxycarbonylpiperidin-4-yl)benzonitrile; 1H NMR (CDCl3) d 1.49 (s, 9H), 1.64 (m, 2H), 1.86 (bd, 2H, J=13.4 Hz), 2.88 (bt, 2H, J=14 Hz), 3.14 (tt, 1H, J=12 Hz, J=4 Hz), 4.27 (bs, 2H), 7.31 (m, 2H), 7.56 (bt, 1H, J=7.7 Hz), 7.63 (bd, 1H, J=7.7 Hz).

후처리

  1. filtrationhydrogenated as above and filtered through celite
  2. customSolvent evaporation

출처 및 근거

ORD 기록
ord-39941b7a8fd549bda75238eeba5982b6
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339090B1

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