Sodium borohydride → HCID 69741154, compound

HRID 1071987Notes

Reaction equation

HRID 1071987 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][CH2:12][N:11]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][CH2:12][NH:11]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69743201HCID 69743201, compound

Product 1

HCID 69741154HCID 69741154, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2-p-fluorophenylethyl)-7-methoxy-3,4-dihydroisoquinoline (1.04 g, 3.67 mmol) in methanol (7 ml) was treated with sodium borohydride (0.56 g, 14.7 mmol) and heated at reflux for one hour. The mixture was cooled and evaporated. The residue was mixed with 1N sodium hydroxide and ethyl acetate and extracted into ethyl acetate. The pooled extracts were washed with saturated sodium chloride, dried, and evaporated to a brown oil (0.59 g, 57%). HPLC-MS (C-18, methanol/water/TFA linear gradient elution, 5 ml/min, 220 nm) single peak at 1.12 min; MS (ES+) obsd m/z=286.34.

Workup

  1. temperatureheated
  2. temperatureat reflux for one hour
  3. temperatureThe mixture was cooled
  4. customevaporated
  5. additionThe residue was mixed with 1N sodium hydroxide and ethyl acetate
  6. extractionextracted into ethyl acetate
  7. washThe pooled extracts were washed with saturated sodium chloride
  8. customdried
  9. customevaporated to a brown oil (0.59 g, 57%)
  10. washHPLC-MS (C-18, methanol/water/TFA linear gradient elution, 5 ml/min, 220 nm) single peak at 1.12 min

Sources & evidence

ORD record
ord-a49ddac55e094275b139d17e912cf437
Source dataset
uspto-grants-2005_06
Patent number
US06908931B2

Reaction notes

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