Pseudoephedrine → N-(1-Hydroxy-1-phenylprop-2-yl)-N-methyl-3-cyclohexylpropionamide

HRID 1532879

반응식

HRID 1532879 반응식
S(Cl)(Cl)=O.[CH:5]1([CH2:11][CH2:12][C:13]([OH:15])=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:16][C@H:17]([NH:26][CH3:27])[C@@H:18]([OH:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[OH:25][CH:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:17]([N:26]([CH3:27])[C:13](=[O:15])[CH2:12][CH2:11][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[CH3:16]

참가 물질

7

반응물 4

HCID 7028PseudoephedrineHCID 24386Thionyl ChlorideHCID 69702Cyclohexanepropanoic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 22014104N-(1-Hydroxy-1-phenylprop-2-yl)-N-methyl-3-cyclohexylpropionamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Thionyl chloride (3.5 mL, 48 mmol) was added to a solution of cyclohexanepropionic acid (5.5 mL, 32 mmol) in CH2Cl2 (60 mL). The mixture was heated at reflux for 60 min and then allowed to cool to ambient temperature and the solvent removed. The residue was redissolved in THF (50 mL) and (1R,2R) pseudoephedrine (4.8 g, 29 mmol) in THF (60 mL) was added to the reaction mixture at 0° C. After stirring for 30 min, a solution of saturated NaHCO3 was added to the mixture which was then extracted with EtOAc. The organic phase was dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes 1:1) to afford an oil which solidified when placed in the refrigerator over night (8.2 g, 94%). MS (CI/NH3) m/z: 304 (M+H)+.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 60 min
  3. customthe solvent removed
  4. dissolutionThe residue was redissolved in THF (50 mL)
  5. extractionwas then extracted with EtOAc
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed (silica gel; EtOAc/hexanes 1:1)
  9. customto afford an oil which
  10. waitplaced in the refrigerator over night

출처 및 근거

ORD 기록
ord-8dc3e0dae8a34193a9b1e7bd443ef552
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06204293B1

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