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

HRID 1468816ノート

反応式

HRID 1468816 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 131709914Lindlars catalyst触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-097bc55351ac4f86b1d82a74a9c4a25a
出典データセット
uspto-grants-2015_04
特許番号
US09006228B2

反応ノート

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