Triphenylphosphine → 2-{2-[6-Allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858087Notes

Reaction equation

HRID 1858087 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH2:48]([C:51]1[CH:52]=[C:53]2[C:58](=[CH:59][C:60]=1[Cl:61])[NH:57][C:56](=[O:62])[C:55]([C:63]1[CH:68]=[C:67]([CH3:69])[CH:66]=[C:65]([CH3:70])[CH:64]=1)=[C:54]2O)[CH:49]=[CH2:50]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:54]1[C:53]2[C:58](=[CH:59][C:60]([Cl:61])=[C:51]([CH2:48][CH:49]=[CH2:50])[CH:52]=2)[NH:57][C:56](=[O:62])[C:55]=1[C:63]1[CH:68]=[C:67]([CH3:69])[CH:66]=[C:65]([CH3:70])[CH:64]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 547112376-allyl-7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one

Product 1

HCID 538248342-{2-[6-Allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl esterYield 80.5%

Procedure

To a solution of 6-allyl-7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one (960 mg in 30 mL of tetrahydrofuran) at 0° C. was added 615 mg of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid tert-butyl ester and 1.04 g of triphenylphosphine followed by 0.56 mL of diethyl azodicarboxylate and the mixture warmed to room temperature. After 20 hours, the solvents were removed in vacuo and the residue purified by flash chromatography on silica gel (hexane:ethylacetate, 85:15; then 80:20; then 90:10) to give the title compound (1.19 g).

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-951900248d7f45dc981ea4aeb6f0b3cb
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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