Cyclohexane, (bromomethyl)- → 1-Cyclohexyl-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one

HRID 916024노트

반응식

HRID 916024 반응식
[CH:1]1([CH2:7]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.[F:14][C:15]1[CH:16]=[CH:17][C:18]([O:33][CH3:34])=[C:19]([C:21]([CH3:32])([CH3:31])[CH2:22][C:23](N2CCOCC2)=[O:24])[CH:20]=1>C1COCC1>[CH:1]1([CH2:7][C:23](=[O:24])[CH2:22][C:21]([C:19]2[CH:20]=[C:15]([F:14])[CH:16]=[CH:17][C:18]=2[O:33][CH3:34])([CH3:32])[CH3:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 137636Cyclohexane, (bromomethyl)-HCID 223985283-(5-Fluoro-2-methoxyphenyl)-3-methyl-1-morpholin-4-ylbutan-1-oneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 223986261-Cyclohexyl-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one수율 58.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

To a solution of cyclohexylmethyl bromide (0.26 g) in THF (1 mL) cooled to −70° C. under argon, tert-butyl lithium (1.7 M in pentane, 1.8 mL) was added dropwise over 5 minutes. The mixture was stirred at −70° C. for 30 minutes. A solution of 3-(5-fluoro-2-methoxyphenyl)-3-methyl-1-morpholin-4-ylbutan-1-one (0.33 g) in THF (1 mL) was added all at once and the mixture was stirred for one hour. The reaction temperature rose to approximately −20° C. The reaction was quenched with EtOH (0.3 mL) and warmed to room temperature. The mixture was diluted with EtOAc, washed with water, dried, filtered, and evaporated. Chromatography of the residue over silica gel (eluent:hexanes to methylene chloride gradient) gave the title compound as an oil (0.2 g).

후처리

  1. stirringwas stirred for one hour
  2. customrose to approximately −20° C
  3. customThe reaction was quenched with EtOH (0.3 mL)
  4. temperaturewarmed to room temperature
  5. additionThe mixture was diluted with EtOAc
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-780270560e3f47b4b49326b01530421f
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268152B2

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