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

HRID 1031487노트

반응식

HRID 1031487 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c33d51057ad54739892d9bc674b95593
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04954502

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