Water → HCID 15082744, compound

HRID 439841Notes

Reaction equation

HRID 439841 reaction equation
[CH3:1][C:2]1([CH3:18])[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C([BH3-])#N.[Na+].O>C(O)(=O)C>[CH3:1][C:2]1([CH3:18])[C@H:17]2[C@H:9]([NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=32)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 15082724HCID 15082724, compound

Product 1

HCID 15082744HCID 15082744, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,10-Dihydro-10,10-dimethylindeno [1,2-b]indole (1.00 g, 4.29 mmol) was reacted with sodium cyanoborohydride (1.0 g, 16 mmol) in glacial acetic acid (20 cm3), for 10 minutes. The solution was poured into water, stirred for 30 minutes, and extracted into diethylether. The organic phase was washed 10 times with water, dried (Na2SO4), and the solvent removed in vacuo. The residue was dissolved in 5% ethylacetate/petrol (60°-80° C.) and filtered through a pad of "flash" silica, yielding, on removal of solvent, a gum which solidified on the oil pump, to give the title compound as a colourless solid. Yield: 0.98 g, (98%) M.p. 57°-59° C. 1H NMR (CDCl3) δ: 1.17 (3H, s,), 1.43 (3H, s,), 3.86 (1H, d,), 3.9 (1H, br,), 5.29 (1H, d,), 6.59 (1H, d,), 6.71 (1H, ddd,), 7.02 (1H, ddd,), 7.2-7.3 (5H, m,).

Workup

  1. extractionextracted into diethylether
  2. washThe organic phase was washed 10 times with water
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in 5% ethylacetate/petrol (60°-80° C.)
  6. filtrationfiltered through a pad of "flash" silica
  7. customyielding, on removal of solvent

Sources & evidence

ORD record
ord-f70faf08720f448aaf318c02247a658e
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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