Quinoline → (Z)-tert-butyl 4-(3-Hydroxyprop-1-enyl)piperidine-1-carboxylate

HRID 1468816노트

반응식

HRID 1468816 반응식
[OH:1][CH2:2][C:3]#[C:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.N1C2C(=CC=CC=2)C=CC=1>CCOC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][CH2:2]/[CH:3]=[CH:4]\[CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

참가 물질

5

반응물 2

HCID 7047QuinolineHCID 69786345Tert-butyl 4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

생성물 1

HCID 90115537(Z)-tert-butyl 4-(3-Hydroxyprop-1-enyl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 131709914Lindlars catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

The alkyne from step B (6.5 g, 27.2 mmol) and quinoline (0.55 mL, 4.62 mmol) were dissolved in EtOAc (120 mL). Lindlar's catalyst (740 mg) was added and the reaction was stirred under hydrogen atmosphere (1 atm) for 40 minutes. The reaction was filtered and concentrated to yield a crude residue which was purified by silica gel chromatography (gradient elution, 0% to 100% EtOAc in hexanes) to yield the desired allylic alcohol. 1H NMR (500 MHz, CDCl3) δ 5.58 (m, 1H), 5.37 (dd, J 10.8 & 9.6 Hz, 1H), 4.22 (d, 2H), 4.16-3.99 (m, 2H), 2.80-2.78 (m, 2H), 2.52-2.40 (m, 1H), 1.61-1.56 (m, 2H), 1.45 (s, 9H), 1.36-1.22 (m, 2H).

후처리

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customto yield a crude residue which
  4. customwas purified by silica gel chromatography (gradient elution, 0% to 100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-097bc55351ac4f86b1d82a74a9c4a25a
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006228B2

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