Sodium borohydride → 2-[4,4-Bis-(4-fluorophenyl)butyl]-1,2,3,4-tetrahydroisoquinolin-5-ol

HRID 1584103Notes

Reaction equation

HRID 1584103 reaction equation
[Br-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:10][CH2:11][CH2:12][N+:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[OH:23])[CH:14]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:22][CH2:21][C:20]3[C:19]([OH:23])=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:14]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 158708912-[4,4-Bis-(4-fluorophenyl)butyl]-5-hydroxyisoquinolinium bromide

Product 1

HCID 158708882-[4,4-Bis-(4-fluorophenyl)butyl]-1,2,3,4-tetrahydroisoquinolin-5-olYield 60.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[4,4-bis-(4-fluorophenyl)-butyl]-5-hydroxyisoquinolinium bromide (4.99 g, 10.61 mmol) in 165 mL of methanol at 0° C. was added sodium borohydride (1.54 g, 40.71 mmol). The reaction mixture was stirred at 0° C. for 15 minutes, then at room temperature for 15 minutes. The mixture was concentrated on a rotavap. The residue was dissolved in ethyl acetate (200 mL) and washed with saturated ammonium chloride solution (150 mL). The organic layer was collected, and the aqueous layer was extracted with ethyl acetate (1×100 mL). The combined organic layers was dried with magnesium sulphate, filtqred, and concentrated to give 1.9 g of crude product as a brown oil. The oil was chromatographed on silica gel eluted with 50% ethyl acetate in hexanes to give 2.54 g of product.

Workup

  1. waitat room temperature for 15 minutes
  2. concentrationThe mixture was concentrated on a rotavap
  3. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with saturated ammonium chloride solution (150 mL)
  5. customThe organic layer was collected
  6. extractionthe aqueous layer was extracted with ethyl acetate (1×100 mL)
  7. dry with materialThe combined organic layers was dried with magnesium sulphate
  8. concentrationconcentrated
  9. customto give 1.9 g of crude product as a brown oil
  10. customThe oil was chromatographed on silica gel
  11. washeluted with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bdaa547f62b044d08041f73cfe73f47f
Source dataset
uspto-grants-1999_08
Patent number
US05932573

Reaction notes

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