Sodium borohydride → HCID 59536265, compound

HRID 445308Notes

Reaction equation

HRID 445308 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59536390HCID 59536390, compound

Product 1

HCID 59536265HCID 59536265, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(3,4-difluorophenyl)-3,4-dihydroisoquinoline (1.34 g, 5.51 mmol) in 20 mL of MeOH, sodium borohydride (0.4366 g, 11.5 mmol) was added. The mixture was stirred for 1 h. MeOH was evaporated and the residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with water and saturated aqueous sodium chloride. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to afford a white solid. The crude product was purified by silica gel chromatography (0-5% iso-propanol (with 10% ammonium hydroxide) in CHCl3) to afford the title compound as a white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 6.99-7.22 (m, 6H) 6.74 (d, J=7.60 Hz, 1H) 5.08 (s, 1H) 3.18-3.32 (m, 1H) 2.96-3.18 (m, 2H) 2.76-2.90 (m, 1H).

Workup

  1. customMeOH was evaporated
  2. customthe residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with water and saturated aqueous sodium chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a white solid
  9. customThe crude product was purified by silica gel chromatography (0-5% iso-propanol (with 10% ammonium hydroxide) in CHCl3)

Sources & evidence

ORD record
ord-79b9066f6cf54f47bd1c1f6979bd652e
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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