Sodium borohydride → 2-Methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine

HRID 563924Notes

Reaction equation

HRID 563924 reaction equation
[CH3:1][C:2]1[S:10][C:9]2[CH2:8][CH2:7][N:6]=[C:5]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[S:10][C:9]2[CH2:8][CH2:7][NH:6][CH:5]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 598200122-Methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-6,7-dihydro-thieno[3,2-c]pyridine

Product 1

HCID 598199942-Methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 740 mg 2-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-6,7-dihydro-thieno[3,2-c]pyridine in 7.4 mL methanol was added portion wise 82 mg (2.17 mmol) NaBH4 at room temperature. The mixture was stirred at room temperature for 30 minutes, cooled in an ice bath and quenched with water and 1N HCl. The methanol was removed in vacuo and the residue stirred in water. The mixture was basified with a 2M Na2CO3 solution and extracted with dichloromethane. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on silica eluting with a gradient formed from heptane and ethyl acetate. The product containing fractions were evaporated to yield 630 mg (87%; over two steps) of the title compound as yellow oil. MS(m/e): 326.1 (MH+).

Workup

  1. temperaturecooled in an ice bath
  2. customquenched with water and 1N HCl
  3. customThe methanol was removed in vacuo
  4. stirringthe residue stirred in water
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified on silica eluting with a gradient
  10. customformed from heptane and ethyl acetate
  11. additionThe product containing fractions
  12. customwere evaporated

Sources & evidence

ORD record
ord-04bc543b5cdb45ab927a4d47ca61b93f
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

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