Sodium cyanoborohydride → HCID 53864285, compound

HRID 439864Notes

Reaction equation

HRID 439864 reaction equation
[F:1][C:2]1[CH:17]=[C:16]2[C:5]([CH2:6][C:7]3[NH:8][C:9]4[C:14]([C:15]=32)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:17]=[C:16]2[C:5]([CH2:6][C@@H:7]3[C@H:15]2[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22408498HCID 22408498, compound

Product 1

HCID 53864285HCID 53864285, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,6-Dihydro-9-fluoroindeno[2,1-b]indole (0.55 g, 2.5 mM) in glacial acetic acid (25 cm3) was stirred and treated with sodium cyanoborohydride (2.1 g, 36.5 mM) in small portions over 10 hours, maintaining the temperature below 18° C. The amount of the reducing agent appears crucial since mixtures form if more is added. The reaction mixture was then added to ice-water (100 cm3) and the yellow oil which was formed was separated from the aqueous phase. The pH of the aqueous phase was then adjusted to 6 by the addition of sodium carbonate (30 g), and the colourless oil which was liberated was extracted into diethyl ether (4×20 cm3). The combined extracts were dried and evaporated to yield an oil which was extracted with hot 60°-80° C. petroleum ether (6×10 cm3) and the residue triturated with ethanol (1 cm3). This treatment caused the compound to crystallise as a colourless prisms which recrystallised from ethanol to give the title compound. Yield: 60 mg, 11% M.p. 116°-117° C.; 1H NMR (CDCl3) δ: 3.06 (1H, dd, J=16.5 and 1.5 Hz), 3.31 (1H, dd, J=16.5 and 6.0 Hz), 3.67 (1H, br.s), 4.70 (1H, d, J=8.0 Hz), 4.82 (1H, ddd, J=8.0, 6.0 and 1.5 Hz), 6.43 (1H, dd, J=8.5 and 4.0 Hz), 6.70 (1H, ddd, J=8.5, 8.5 and 2.5 Hz), 7.07 (1H, dd, J=8.5 and 2.5 Hz), 7.16-7.25 (3H, m), 7.33 (1H, m).

Workup

  1. temperaturemaintaining the temperature below 18° C
  2. customform
  3. additionif more is added
  4. customthe yellow oil which was formed
  5. customwas separated from the aqueous phase
  6. additionThe pH of the aqueous phase was then adjusted to 6 by the addition of sodium carbonate (30 g)
  7. extractionthe colourless oil which was liberated was extracted into diethyl ether (4×20 cm3)
  8. customThe combined extracts were dried
  9. customevaporated
  10. customto yield an oil which
  11. extractionwas extracted with hot 60°-80° C. petroleum ether (6×10 cm3)
  12. customthe residue triturated with ethanol (1 cm3)
  13. customto crystallise as a colourless prisms which
  14. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-083e63a69abb4717a340fa3cdf865b69
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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