Sodium borohydride → HCID 22391008, compound

HRID 1071988Notes

Reaction equation

HRID 1071988 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][C:16]4[O:22][CH2:21][O:20][C:17]=4[CH:18]=3)[CH2:13][CH2:12][N:11]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]2[C:19]3[C:14](=[CH:15][C:16]4[O:22][CH2:21][O:20][C:17]=4[CH:18]=3)[CH2:13][CH2:12][NH:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22391012HCID 22391012, compound

Product 1

HCID 22391008HCID 22391008, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2-p-fluorophenylethyl)-6,7-methylenedioxy-3,4-dihydroisoquinoline (0.78 g, 2.67 mmol) in methanol (7 ml) was treated with sodium borohydride (0.30 g, 8.01 mmol) and heated at reflux for two hours. 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 pale yellow oil (0.56 g, 70%). 1H NMR (CDCl3) δ 7.18 (m, 2 H); 6.97 (m, 2 H); 6.58 (m, 2 H), 5.88 (s, 2 H); 3.90 (m, 1 H); 3.21 (m, 1 H); 2.99 (m, 1 H); 2.81-2.62 (m, 4 H); 2.06 (m, 2 H). HPLC-MS (C-18, methanol/water/TFA linear gradient elution, 5 ml/min, 220 nm) single peak at 1.13 min; MS (ES+) obsd m/z=299.87.

Workup

  1. temperatureheated
  2. temperatureat reflux for two hours
  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 pale yellow oil (0.56 g, 70%)
  10. washHPLC-MS (C-18, methanol/water/TFA linear gradient elution, 5 ml/min, 220 nm) single peak at 1.13 min

Sources & evidence

ORD record
ord-a96d573522914e70b3c24c0a782aad39
Source dataset
uspto-grants-2005_06
Patent number
US06908931B2

Reaction notes

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