Water → 7-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepin-4-ol

HRID 1511618Notes

Reaction equation

HRID 1511618 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([N:5]1[CH2:11][CH2:10][CH:9]([OH:12])[C:8]2[CH:13]=[CH:14][O:15][C:7]=2[CH2:6]1)=O.B.O>C1COCC1>[F:17][C:2]([F:1])([F:16])[CH2:3][N:5]1[CH2:11][CH2:10][CH:9]([OH:12])[C:8]2[CH:13]=[CH:14][O:15][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 866392267-Trifluoroacetyl-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepin-4-ol

Product 1

HCID 684100197-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7-Trifluoroacetyl-5,6,7,8-tetrahydro-4H-furo[2,3-c]-azepin-4-ol prepared in the step 1 was dissolved in 1 mL of THF, a three molar equivalent of a solution of borane in THF was dropped thereinto under ice-cooling with stirring and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured over 1 mL of water followed by extracting with ethyl acetate. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The resulting residue was purified by silica gel column chromatography to give 23 mg of the objective compound.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-653463ebc30a4d3399c7859dc5485df6
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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