3,4-dihydro-2H-pyran → 5-(Tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin

HRID 1416356노트

반응식

HRID 1416356 반응식
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:7]2.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[CH2:7]2

참가 물질

5

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 154910662-Trifluoroacetyl-1,2,3,4-tetrahydro-5-isoquinolinol

생성물 1

HCID 154342975-(Tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3.7 g (15.9 mmol) of 5-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (Example 1) and 4.4 mL (47.7 mmol) 2,3-dihydropyrane were dissolved in dichloromethane and catalytic amount of p-toluenesulfonic acid monohydrate was added. After completion of the reaction (System A), the reaction mixture was diluted with dichloromethane, washed with water and aqueous sodium chloride. The solution was dried over Na2SO4, evaporated to dryness, and the product was purified by silicagel chromatography (System A). Yield 4.13 g, 79%. 1H NMR (CDCl3, 400 MHz): 7.16 (1H, m), 7.00 (1H, m), 6.77 (1H, m), 5.45 (1H, m), 4.79 (2H, ss), 3.8 (3H, m), 3.6 (1H, m), 2.9 (4H, m).

후처리

  1. customAfter completion of the reaction (System A), the reaction mixture
  2. washwashed with water and aqueous sodium chloride
  3. dry with materialThe solution was dried over Na2SO4
  4. customevaporated to dryness
  5. customthe product was purified by silicagel chromatography (System A)

출처 및 근거

ORD 기록
ord-b889aade26804b538c19425e381f7305
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912342

반응 노트

불러오는 중…