Hydrochloric Acid → HCID 70453900, compound

HRID 2290923Notes

Reaction equation

HRID 2290923 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@@H:8]([C:9](=O)[NH:10][CH2:11]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH3:18].B.C1COCC1.[ClH:25]>C1COCC1>[ClH:25].[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@@H:8]([CH2:9][NH:10][CH2:11]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 2723981Borane;tetrahydrofuranHCID 13746076HCID 13746076, compound

Product 1

HCID 70453900HCID 70453900, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans-3a,4,5,9b-tetrahydro-6,7-dimethoxy-1H-benz[e]isoindole-1-(2H)-one and 15 mL dry THF was stirred under N2 at 0° as BH3.THF (27.3 mL, 1M solution) was added slowly. The reaction mixture was stirred at reflux for 2.5 hours, was cooled to 0°, and 30 mL methanolic HCl was added cautiously. The solution was stirred at reflux for 1 hour, then was evaporated to dryness. Water was added and the aqueous layer was extracted with ether. After basifying (1N KOH), the aqueous layer was extracted with ether. The combined basic extracts were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield a clear oil which was converted to the HCl salt (ethereal HCl), evaporated, dried (in-vacuo) to obtain a white solid which was triturated with ether to yield 1.03 g cream colored solid, (63%); mp 196°-8°; M+ 233.

Workup

  1. additionwas added slowly
  2. temperatureat reflux for 2.5 hours
  3. temperaturewas cooled to 0°
  4. stirringThe solution was stirred
  5. temperatureat reflux for 1 hour
  6. customwas evaporated to dryness
  7. additionWater was added
  8. extractionthe aqueous layer was extracted with ether
  9. extractionthe aqueous layer was extracted with ether
  10. washThe combined basic extracts were washed with water, saturated aqueous NaCl
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customevaporated
  14. customto yield a clear oil which
  15. customevaporated
  16. customdried (in-vacuo)
  17. customto obtain a white solid which
  18. customwas triturated with ether
  19. customto yield 1.03 g cream colored solid, (63%)

Sources & evidence

ORD record
ord-b876e7ef0a9c428ebf32cbac7209e10b
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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