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Pyridine → rac-(3R*,5S*)-3-chloro-5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

HRID 594401
ノート
印刷プレビュー

反応式

HRID 594401 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[C:14](=[O:28])[CH:13](O)[CH2:12]1.O=S(Cl)[Cl:32].N1C=CC=CC=1>O1CCOCC1>[Cl:32][CH:13]1[CH2:12][CH:11]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=2[O:9][CH3:10])[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[C:14]1=[O:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 69082591rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

生成物 1

HCID 69081638rac-(3R*,5S*)-3-chloro-5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A solution of rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)-benzyl)pyrrolidin-2-one (200 mg; 0.48 mmol) in dioxane (1 ml) was treated at rt successively with SOCl2 (69 mg; 0.58 mmol) and pyridine (46 mg; 0.58 mmol). The resulting mixture was then heated to 80° C. for 3 h. After cooling to rt, the mixture was concentrated under reduced pressure before water and AcOEt were added. The separated organic layer was washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=50/1) afforded rac-(3R*,5S*)-3-chloro-5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one as a pale yellow solid. LC-MS (conditions A): tR=0.95 min.; [M+H]+: 430.20 g/mol.

後処理

  1. temperatureAfter cooling to rt
  2. concentrationthe mixture was concentrated under reduced pressure before water and AcOEt
  3. additionwere added
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=50/1)

出典と根拠

ORDレコード
ord-c4ff4f5e366f401faa452660eecdbda0
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242970B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート