Sodium borohydride → HCID 67369877, compound

HRID 383985Notes

Reaction equation

HRID 383985 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[C:11]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1>CCO>[F:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH:11]2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67367547HCID 67367547, compound

Product 1

HCID 67369877HCID 67369877, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.65 g (17.1 mmol) of NaBH4 were added in portions to a solution of 3.2 g (max. 14.2 mmol) of the crude product 7-fluoro-1-phenyl-3,4-dihydroisoquinoline in EtOH (80 ml) and the mixture was then stirred for 16 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with DCM (200 ml). It was washed with water and the aqueous phase was extracted with DCM (2×150 ml). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 7-Fluoro-1-phenyl-1,2,3,4-tetrahydroisoquinoline was obtained as the crude product, which was reacted further with no additional purification.

Workup

  1. concentrationThen the mixture was concentrated to small volume under vacuum
  2. washIt was washed with water
  3. extractionthe aqueous phase was extracted with DCM (2×150 ml)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-4138668e6cef4e1d9b10c6c7ce60c519
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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