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 1857633ノート

反応式

HRID 1857633 の反応式
[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]

参加物

5

反応物 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

生成物 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 ester収率 80.5%

実験手順

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:ethyl acetate, 85:15; then 80:20; then 90:10) to give 1.19 g of the title compound.

後処理

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

出典と根拠

ORDレコード
ord-a8df66b2c35541c3ac637b95cdcbe6ed
出典データセット
uspto-grants-2000_11
特許番号
US06147088

反応ノート

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