2-Bromo-3-methoxypyridine → 2-(3-methoxy-2-pyridinyl)-5-phenylmethyl-(1S,4S)-2,5-diazabicyclo[2.2.1]-heptane

HRID 1031487ノート

反応式

HRID 1031487 の反応式
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:10]([N:17]1[CH2:22][C@@H:21]2[CH2:23][C@H:18]1[CH2:19][NH:20]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH3:9][O:8][C:7]1[C:2]([N:20]2[CH2:19][C@@H:18]3[CH2:23][C@H:21]2[CH2:22][N:17]3[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 903642-Bromo-3-methoxypyridineHCID 14612543(1S,4S)-2-Benzyl-2,5-Diazabicyclo[2.2.1]heptane

生成物 1

HCID 186409522-(3-methoxy-2-pyridinyl)-5-phenylmethyl-(1S,4S)-2,5-diazabicyclo[2.2.1]-heptane収率 51%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-bromo-3-methoxy pyridine (9.9 g) and (1S,4S)-N-benzyl-2,5-diazabicyclo[2.2.1]heptane (10.9 g) was heated at 100° C. in a Parr bomb for 67 h. The reaction mixture was cooled to 23° C., dissolved in CH2Cl2, extracted with 5% NaHCO3, and finally wit:h H2O. The organic layer was dried over K2CO3, filtered, and concentrated under reduced pressure. The crude oil was purified by silica gel chromatography (CH2Cl2 :MeOH; 96:4) to give the desired product (7.93 g, 51%).

後処理

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. extractionextracted with 5% NaHCO3, and finally wit
  3. dry with materialThe organic layer was dried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude oil was purified by silica gel chromatography (CH2Cl2 :MeOH; 96:4)

出典と根拠

ORDレコード
ord-c33d51057ad54739892d9bc674b95593
出典データセット
uspto-grants-1990_09
特許番号
US04954502

反応ノート

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