Acetonitrile → HCID 23506040, compound

HRID 1281281Notes

Reaction equation

HRID 1281281 reaction equation
CC#N.[F:4][C:5]([F:10])([F:9])[CH:6]1[O:8][CH2:7]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].[O:36]([C:43]1[CH:44]=[C:45]([CH2:49][C:50]([NH:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([C:64]3[CH:68]=[CH:67][O:66][CH:65]=3)[CH:59]=2)(O)C(F)(F)F)C=C[CH:48]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(OCC)C.CCO>[O:36]([C:43]1[CH:48]=[C:50]([N:56]([CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([C:64]3[CH:68]=[CH:67][O:66][CH:65]=3)[CH:59]=2)[CH2:7][CH:6]([OH:8])[C:5]([F:10])([F:9])[F:4])[CH:49]=[CH:45][CH:44]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 5207692-(Trifluoromethyl)oxirane2×HCID 2733225Ytterbium triflate2×HCID 131723493HCID 131723493, compound

Product 1

HCID 23506040HCID 23506040, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a CH3CN (2 mL) solution of amine (0.20 g, 0.58 mmol) from EX-601B was added 1,1,1-trifluoro-2,3-epoxypropane (0.10 mL, 1.2 mmol) and Yb(OTf)3 (0.035 g, 0.056 mmol). The cloudy solution was stiffed in a sealed flask at 40° C. After 18 h, additional 1,1,1-trifluoro-2,3-epoxypropane (0.20 mL, 2.4 mmol) and Yb(OTf)3 (0.035 g, 0.056 mmol) were added, and the mixture was heated an additional 4 h. 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 10% ethyl acetate in hexane gave an oil which was dissolved in EtOH, stripped and dried in vacuo to give 0.14 g (53%) of the desired 3[(3-phenoxyphenyl) [[(3-(3-furanyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol product as a colorless oil, >99% pure by HPLC analysis. Anal. calcd. for C26H22NO3F3.0.3 EtOH:

Workup

  1. customThe cloudy solution was stiffed in a sealed flask at 40° C
  2. temperaturethe mixture was heated an additional 4 h.
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated to an oil
  6. customPurification by flash chromatography on silica gel eluting with 10% ethyl acetate in hexane
  7. customgave an oil which
  8. customdried in vacuo
  9. customto give 0.14 g (53%) of the

Sources & evidence

ORD record
ord-4afc46a24bbc42eb82f3b55b70f476f4
Source dataset
uspto-grants-2002_09
Patent number
US06451823B1

Reaction notes

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