Sodium borohydride → 1-(4-Trifluoromethoxyphenyl)-1,2,3,4-tetrahydro-isoquinoline

HRID 567113Notes

Reaction equation

HRID 567113 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][N:11]=2)=[CH:6][CH:5]=1.[BH4-].[Na+]>CO>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][NH:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 212643761-(4-Trifluoromethoxyphenyl)-3,4-dihydro-isoquinoline

Product 1

HCID 212644061-(4-Trifluoromethoxyphenyl)-1,2,3,4-tetrahydro-isoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above 1-(4-trifluoromethoxyphenyl)-3,4-dihydro-isoquinoline (0.40 g, 1.4 mmol) was dissolved in methanol (20 mL) and sodium borohydride (0.08 g, 2.1 mmol) was added slowly. The reaction mixture was stirred at room temperature for 2.5 hours. The mixture was evaporated in vacuo, redissolved in 1 N NaOH (20 mL) and extracted with dichloromethane (50 mL). The organic phase was dried (MgSO4), filtered and evaporated in vacuo. The remaining oil (0.35 g) was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (9:1). This afforded 0.56 g (56%) of the title compound.

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionredissolved in 1 N NaOH (20 mL)
  3. extractionextracted with dichloromethane (50 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe remaining oil (0.35 g) was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (9:1)

Sources & evidence

ORD record
ord-3315afc3abdf4e7aac800e6cc6432e12
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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