Tryptophol → HCID 44224247, 화합물

HRID 2066958

반응식

HRID 2066958 반응식
[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH:5]([CH3:10])[CH2:4]1.[CH:18]1[CH:19]=[CH:20][C:21]2[NH:26][CH:25]=[C:24]([CH2:27][CH2:28]O)[C:22]=2[CH:23]=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>C(Cl)Cl.C(O)C.O>[CH3:17][N:2]([CH3:1])[C:3]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][C:6]2([C:25]3[NH:26][C:21]4[C:22]([C:24]=3[CH2:27][CH2:28][O:9]2)=[CH:23][CH:18]=[CH:19][CH:20]=4)[CH:5]([CH3:10])[CH2:4]1

참가 물질

8

반응물 4

HCID 10685TryptopholHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 67408596(+/-)-4-Dimethylamino-2-methyl-4-phenylcyclohexanone

생성물 1

HCID 44224247HCID 44224247, 화합물

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

(±)-4-dimethylamino-2-methyl-4-phenylcyclohexanone (461 mg, 2 mmol) together with tryptophol (322 mg, 2 mmol) was dissolved in DCM (100 ml) and mixed with trifluoromethane sulphonic acid (0.19 ml, 2.14 mmol). The mixture was stirred at RT for 20 h. The reaction mixture was mixed with 2N NaOH (2 ml) and H2O (2 ml) and stirred for 20 min. The organic residue was firstly washed with 2N NaOH (5 ml), then with H2O (5 ml) and dried over Na2SO4. The solvent was then removed in vacuum. The semisolid residue obtained was taken up in 10 ml of ethanol and cooled to 5° C. for 2 h. The solid precipitated out during this was discarded. The residue remaining in the mother liquor was purified by column chromatography on silica gel (50 g, EE/ethanol=4:1).

후처리

  1. stirringstirred for 20 min
  2. washThe organic residue was firstly washed with 2N NaOH (5 ml)
  3. dry with materialwith H2O (5 ml) and dried over Na2SO4
  4. customThe solvent was then removed in vacuum
  5. customThe semisolid residue obtained
  6. temperaturecooled to 5° C. for 2 h
  7. customThe solid precipitated out during
  8. customwas purified by column chromatography on silica gel (50 g, EE/ethanol=4:1)

출처 및 근거

ORD 기록
ord-5ec71cc0884547ada054ee4e6bb528a7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293758B2

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