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

HRID 963983Notes

Reaction equation

HRID 963983 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, filtered, 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. filtrationfiltered
  9. concentrationconcentrated
  10. customto give 1.9 g of crude product as a brown oil
  11. customThe oil was chromatographed on silica gel
  12. washeluted with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d9f2ac091fd34998a6b866074fb20297
Source dataset
uspto-grants-1998_06
Patent number
US05767129

Reaction notes

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