Tetrahydrofuran → tert-Butyl (2R,3R)-3-{benzyl[(1R)-1-phenylethyl]amino}-2-hydroxy-3-phenylpropanoate

HRID 1823837노트

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HRID 1823837 반응식
[CH2:1]([NH:8][C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22]([O:26][C:27](=[O:36])[CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:25])([CH3:24])[CH3:23].[Cl-].[NH4+].[O:39]1CCCC1>CCCCCC>[CH2:1]([N:8]([C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C@H:29]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@@H:28]([OH:39])[C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 347555Tert-butyl cinnamateHCID 1268086(+)-BenzylphenethylamineHCID 178418339Butyllithium

생성물 1

HCID 10477875tert-Butyl (2R,3R)-3-{benzyl[(1R)-1-phenylethyl]amino}-2-hydroxy-3-phenylpropanoate

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
-78 °C

실험 절차

To a solution of (1R)-N-benzyl-1-phenyl-1-ethanamine (16.6 g, 79 mmol) in tetrahydrofuran (200 ml) at −10° C. was added n-butyl lithium (46 ml of a 1.6M solution in hexane, 74 mmol) dropwise. The purple solution was stirred for 15 minutes, cooled to −78° C. and a solution of tert-butylcinnamate (10.0 g, 49 mmol) in tetrahydrofuran (100 ml) added dropwise. After stirring for 2 hours (−)-camphorsulphonyl oxaziridine (18 g, 79 mmol) was added portionwise and the reaction stirred at −78° C. for 1 hour. The reaction was warmed to room temperature and saturated aqueous ammonium chloride solution added and the solvent removed under reduced pressure. The remaining aqueous mixture was extracted with dichloromethane (x2) and the combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure. The residue was dissolved in diethyl ether, filtered and the filtrate washed with water, dried (MgSO4), filtered and evaporated under reduced pressure. The pale yellow oily residue was purified by column chromatography on silica gel using a gradient elution of diethyl ether:hexane (0:100 to 10:90) to afford the title compound as a colourless oil, 10.0 g.

후처리

  1. additionwas added portionwise
  2. stirringthe reaction stirred at −78° C. for 1 hour
  3. temperatureThe reaction was warmed to room temperature
  4. customthe solvent removed under reduced pressure
  5. extractionThe remaining aqueous mixture was extracted with dichloromethane (x2)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. dissolutionThe residue was dissolved in diethyl ether
  10. filtrationfiltered
  11. washthe filtrate washed with water
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. customevaporated under reduced pressure
  15. customThe pale yellow oily residue was purified by column chromatography on silica gel using
  16. washa gradient elution of diethyl ether:hexane (0:100 to 10:90)

출처 및 근거

ORD 기록
ord-d696d5b001e849d79ef0e8beae393dc6
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041667B1

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