ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethyl Sulfoxide → (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde

HRID 2186384
ノート
印刷プレビュー

反応式

HRID 2186384 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][C@@H:14]1[C@H:19]([CH2:20][CH2:21][CH:22]([OH:35])[C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17][N:16]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:15]1.C(N(CC)CC)C>ClCCl>[O:35]=[C:22]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[CH2:21][CH2:20][C@@H:19]1[CH2:18][CH2:17][N:16]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:15][C@@H:14]1[CH2:13][CH:12]=[O:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69353248(3R,4R)-3-(2-hydroxyethyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine

生成物 1

HCID 86758164(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde収率 100.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒4 回

実験手順

A mixture of 13.7 g of dimethyl sulfoxide in 65 cm3 of dichloromethane was slowly added, with stirring and under an inert atmosphere, to a solution, cooled to a temperature in the region of −60° C., of 8.3 cm3 of oxalyl chloride in 65 cm3 of dichloromethane. After stirring the mixture for 15 minutes, 10 g of (3R,4R)-3-(2-hydroxyethyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine, dissolved in 65 cm3 of dichloromethane, were slowly added. After stirring the mixture for 30 minutes, 61.7 cm3 of triethylamine, dissolved in 65 cm3 of dichloromethane, were finally added dropwise. The mixture was stirred for a further 3 hours at approximately −60° C. and then poured onto 400 cm3 of ice-cold water. After separating the mixture by settling, the organic phase was washed with 400 cm3 of a 10% (by mass) aqueous citric acid solution and then dried over magnesium sulfate, filtered, and evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 9.95 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde were obtained in the form of an. oil with a brown color.

後処理

  1. additionwas slowly added
  2. stirringAfter stirring the mixture for 15 minutes
  3. additionwere slowly added
  4. stirringAfter stirring the mixture for 30 minutes
  5. additionwere finally added dropwise
  6. stirringThe mixture was stirred for a further 3 hours at approximately −60° C.
  7. customAfter separating the mixture
  8. washthe organic phase was washed with 400 cm3 of a 10% (by mass) aqueous citric acid solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

出典と根拠

ORDレコード
ord-ee99234dfd8844c2b160c69c4cf0bf66
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06403610B1

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート