Sodium borohydride → HCID 13150100, compound

HRID 369985Notes

Reaction equation

HRID 369985 reaction equation
[CH2:1]1[C:13]2[N:4]([C:5](=O)[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH:12]=2)[CH2:3][CH2:2]1.[BH4-].[Na+]>P(Cl)(Cl)(Cl)=O.CO>[CH2:1]1[CH:13]2[N:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 12730635HCID 12730635, compound

Product 1

HCID 13150100HCID 13150100, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2,3-dihydropyrrolo[1,2-b]isoquinolin-5(1H)-one (10.8 g, 58.3 mmol) [G. M. Coppola, J. Heterocycl. Chem., 181, 18, 767] in phosphorus oxychloride (100 ml) was heated at reflux for 1.5 h. Upon cooling, the solvent was removed in vacuo to give an oil. This oil was immediately taken up in cold methanol (275 ml) and sodium borohydride (4.0 g) was added portionwise to this solution while maintaining the reaction mixture at 0° C. The solvent was concentrated and the residue was dissolved in water and washed twice with ethyl acetate. The aqueous solution was made basic with potassium carbonate solution and extracted with ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated to give an oil. Column chromatography on silica gel gave unreacted starting material (3.57 g, 36%) and the title compound (4.2 g, 63% based on recovered starting material) as a light oil; MS 174 (M+H)+ ; NMR (CDCl3) 7.0-7.2 (broad m, 4H), 4.13 (d, 1H, J=15), 3.40 (d, 1H, J=15), 3.27 (dt, 1H), 2.9-3.1 (M, 1H), 2.71 (t, 1H), 1.4-2.4 (m, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. temperatureUpon cooling
  4. customthe solvent was removed in vacuo
  5. customto give an oil
  6. concentrationThe solvent was concentrated
  7. dissolutionthe residue was dissolved in water
  8. washwashed twice with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic phase was dried (magnesium sulfate)
  11. concentrationconcentrated
  12. customto give an oil
  13. customColumn chromatography on silica gel gave unreacted

Sources & evidence

ORD record
ord-77acc4a6dc344e76a21b27dd9c651f9a
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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