Water → N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(2-fluorophenyl)ethanamine

HRID 851171노트

반응식

HRID 851171 반응식
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)([O:3]C)=O.[OH:17][CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])[CH2:19][NH2:20].O>C1C=CC=CC=1>[OH:3][CH2:1][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:20][CH2:19][CH:18]([OH:17])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH3:15])=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetateHCID 150671762-Amino-1-(2-fluorophenyl)ethan-1-ol

생성물 1

HCID 13079624N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(2-fluorophenyl)ethanamine

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of 1-(4-carbomethoxymethoxyphenyl)propan-2-one (2.22 g) and 2-hydroxy-2-(2-fluorophenyl)ethanamine (1.55 g) in benzene (100 ml) was boiled under reflux with azeotropic removal of water using a Dean and Stark trap, for 2 hours. The solution was cooled, evaporated to dryness, the residue dissolved in methanol and sodium borohydride (500 mg) added. After 30 minutes, the methanol was evaporated and the residue partitioned between ethyl acetate and water. The organic layer was dried (magnesium sulphate) and evaporated to leave an oil which was chromatographed on silica gel 60 eluting with 2% methanol/chloroform. N-[2-(4-(2-hydroxyethoxy)phenyl-1-methylethyl]-2-hydroxy-2-(2-fluorophenyl)ethanamine (300 mg) crystallised from hexane, m.p. 80°-95°, as a 55:45 mixture of diastereoisomers.

후처리

  1. temperatureThe solution was cooled
  2. customevaporated to dryness
  3. dissolutionthe residue dissolved in methanol
  4. additionsodium borohydride (500 mg) added
  5. waitAfter 30 minutes
  6. customthe methanol was evaporated
  7. customthe residue partitioned between ethyl acetate and water
  8. dry with materialThe organic layer was dried (magnesium sulphate)
  9. customevaporated
  10. customto leave an oil which
  11. customwas chromatographed on silica gel 60 eluting with 2% methanol/chloroform
  12. customN-[2-(4-(2-hydroxyethoxy)phenyl-1-methylethyl]-2-hydroxy-2-(2-fluorophenyl)ethanamine (300 mg) crystallised from hexane, m.p. 80°-95°, as a 55:45 mixture of diastereoisomers

출처 및 근거

ORD 기록
ord-2339547bef55412f994753969116a060
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382958

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