Triphenylphosphine → tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yloxy)piperidine-1-carboxylate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:34][C:35]1[CH:44]=[C:43]2[C:38]([CH2:39][CH2:40][C:41](=[O:45])[NH:42]2)=[CH:37][CH:36]=1.[C:46]([O:50][C:51]([N:53]1[CH2:58][CH2:57][CH:56](O)[CH2:55][CH2:54]1)=[O:52])([CH3:49])([CH3:48])[CH3:47]>O1CCCC1>[O:45]=[C:41]1[CH2:40][CH2:39][C:38]2[C:43](=[CH:44][C:35]([O:34][CH:56]3[CH2:57][CH2:58][N:53]([C:51]([O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:52])[CH2:54][CH2:55]3)=[CH:36][CH:37]=2)[NH:42]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Triphenylphosphine (0.577 g, 2.2 mmol) was dissolved in dry tetrahydrofuran (20 mL) under argon and the solution cooled to 0–5° C. Diisopropyl azodicarboxylate (0.404 g, 2 mmol) was added dropwise and the mixture stirred at 0–5° C. for 20 min. before addition of 7-hydroxy-3,4-dihydro-1H-quinolin-2-one (0.326 g, 2 mmol) and 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (0.402 g, 2 mmol). The resulting mixture was stirred at ambient temperature for 18 h then evaporated to dryness under reduced pressure. Chromatography on SiO2, eluting with a gradient of ethyl acetate in 60–80° C. petroleum ether, gave the title compound (0.2 g, 29%) as a white solid.
Workup
- temperaturethe solution cooled to 0–5° C
- customthen evaporated to dryness under reduced pressure
- washChromatography on SiO2, eluting with a gradient of ethyl acetate in 60–80° C. petroleum ether
Sources & evidence
- ORD record
- ord-9a923ae1eea44fb293a53fe57e4be0a3
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07244726B2
Reaction notes
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