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

HRID 1468816Notes

Reaction equation

HRID 1468816 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-097bc55351ac4f86b1d82a74a9c4a25a
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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