Ethanol → HCID 68831649, compound

HRID 1246562Notes

Reaction equation

HRID 1246562 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.F[B-](F)(F)F.[Li+].[C:16](#[N:18])[CH3:17].[C:19]([OH:28])(=[O:27])[C@@H:20]([C@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21].[CH2:29]([OH:31])[CH3:30]>O>[C:24]([C@@H:22]([C@H:20]([C:19]([OH:28])=[O:27])[OH:21])[OH:23])([OH:26])=[O:25].[S:1]1[C:9]2[CH2:8][CH2:7][N:6]([CH2:20][C@@H:22]([OH:23])[CH2:24][O:26][C:4]3[CH:9]=[CH:8][CH:7]=[C:17]([C:16]4[C:30]5[S:1][CH:2]=[CH:3][C:29]=5[O:31][N:18]=4)[CH:5]=3)[CH2:5][C:4]=2[CH:3]=[CH:2]1

Participants

7

Reactant 5

HCID 702EthanolHCID 6342AcetonitrileHCID 444305L-Tartaric acidHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridineHCID 4298216Lithium tetrafluoroborate

Product 1

HCID 68831649HCID 68831649, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a solution of the example 4 epoxide (0.79 g, 0.0029 mol), 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine free base (0.40 g, 0.0029 mol), lithium tetrafluoroborate (0.27 g, 0.0029 mol) and acetonitrile (50 mL) overnight at room temperature. Pour into water (300 mL) and extract with ethyl acetate. Dry (Na2SO4), filter and concentrate the organic phase, and purify the residue by flash chromatography (silica gel, elute with 3% methanol in dichloromethane) to afford a yellow oil. Dissolve the oil in ethanol, treat with L-tartaric acid (1 molar equivalent), heat to afford a solution, and cool and collect the title compound (0.34 g, 21%) as crystals, m.p. 81–83° C.

Workup

  1. extractionextract with ethyl acetate
  2. dry with materialDry (Na2SO4)
  3. filtrationfilter
  4. concentrationconcentrate the organic phase
  5. custompurify the residue
  6. washby flash chromatography (silica gel, elute with 3% methanol in dichloromethane)
  7. customto afford a yellow oil
  8. temperatureheat
  9. customto afford a solution
  10. temperaturecool
  11. customcollect the title compound (0.34 g, 21%) as crystals, m.p. 81–83° C.

Sources & evidence

ORD record
ord-5f4bcc4ee3494bb98b45189b9750f346
Source dataset
uspto-grants-2006_10
Patent number
US07125903B1

Reaction notes

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