Acetonitrile → 3-[(3-Phenoxyphenyl)[[3-(tetrahydro-2-furanyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol

HRID 990534노트

반응식

HRID 990534 반응식
CC#N.[O:4]([C:11]1[CH:12]=[C:13]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]3[CH2:29][CH2:28][CH2:27][O:26]3)[CH:20]=2)[CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:30][C:31]([F:36])([F:35])[CH:32]1[O:34][CH2:33]1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>C(OCC)C.CCO>[O:4]([C:11]1[CH:12]=[C:13]([N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]3[CH2:29][CH2:28][CH2:27][O:26]3)[CH:20]=2)[CH2:33][CH:32]([OH:34])[C:31]([F:36])([F:35])[F:30])[CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 5207692-(Trifluoromethyl)oxiraneHCID 2733225Ytterbium triflateHCID 23506095N-(3-phenoxyphenyl)-[[3-(tetrahydro-2-furanyl)phenyl]methyl]amine

생성물 1

HCID 235060483-[(3-Phenoxyphenyl)[[3-(tetrahydro-2-furanyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol수율 30.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

반응 조건

온도
40 °C

실험 절차

To a CH3CN (1 mL) solution of the amine (0.32 g, 0.93 mmol) from EX-608E was added 1,1,1-trifluoro-2,3-epoxypropane (0.24 mL, 2.8 mmol) and Yb(OTf)3 (0.115 g, 0.18 mmol). The cloudy solution was stirred in a sealed flask at 40° C. for 18 h. The cooled reaction mixture was diluted with diethyl ether and washed with water and brine. The organic layer was dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane gave an oil which was dissolved in EtOH, stripped and dried in vacuo to give 0.13 g (30%) of the desired 3-[(3-phenoxyphenyl)[[3-(tetrahydro-2-furanyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol product as a colorless oil. Anal. calcd. for C26H26NO3F3.0.5 EtOH: C, 67.33; H, 6.04; N, 2.94. Found: C, 67.49; H, 6.08; N, 2.91. HRMS calcd. 458.1943 [M+H]+, found: 458.1937. 1H NMR (C6D6) δ0.45 (d, 1H), 1.43 (m, 3H), 1.79 (m, 1H), 1.99 (m, 1H), 3.24 (m, 1H), 3.43 (m, 1H), 3.76 (m, 2H), 4.24 (s, 2H), 4.60 (t, 1H), 6.35 (m, 1H), 6.43 (dd, 1H), 6.54 (dd, 1H), 6.8 (m, 2H), 6.9-7.0 (m, 7H), 7.15 (d, 1H).

후처리

  1. customThe cooled reaction mixture
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated to an oil
  5. customPurification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane
  6. customgave an oil which
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-c51ff725fa2742959f36e1f04ac9e589
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458852B1

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