Diethyl Ether → 3-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yloxy)-8-methyl-8-azabicyclo[3.2.1]octane

HRID 2094569

반응식

HRID 2094569 반응식
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:3]1[CH2:4][CH2:5]2.[Li]CCCC.[Cl:16][C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:18]=1.CCOCC>C1COCC1>[Cl:16][C:17]1[N:18]=[C:19]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[N:20]=[C:21]([O:10][CH:8]2[CH2:9][CH:3]3[N:2]([CH3:1])[CH:6]([CH2:5][CH2:4]3)[CH2:7]2)[N:22]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 178418339Butyllithium

생성물 1

HCID 872396073-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yloxy)-8-methyl-8-azabicyclo[3.2.1]octane수율 42%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

In a three neck flask equipped with stirring bar under N2 atmosphere tropine (1 g, 4.24 mmol) was suspended in (anhydrous) THF (15 mL). The mixture was cooled to −78° C. and BuLi (2M in THF) (5.53 ml, 1.2 eq) was added dropwise and the mixture was allowed to warm to 25° C. over 30 minutes. To the reaction mixture 2,4,-dichloro-6-morpholin-4-yl-[1,3,5]triazine (996 mg, 4,24, mmole) was added and allowed to stir overnight. For work up, ether (100 mL) was added. The organic layer was washed with water (20 mL) and brine (20 mL) and dried over MgSO4. filtered and the solvents were removed to obtain a colorless oil. Further purification by flash-chromatography using CH2Cl2/MeOH/NH3 (15:1:0.1) gave the product as white solid (600 mg, 42% yield); MS (ESI) m/z 340

후처리

  1. customIn a three neck flask equipped
  2. temperatureto warm to 25° C. over 30 minutes
  3. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed
  7. customto obtain a colorless oil
  8. customFurther purification by flash-chromatography

출처 및 근거

ORD 기록
ord-1038fdff418244c5901cae86f6bc11a9
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445486B2

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