Sodium cyanoborohydride → HCID 54539506, compound

HRID 439863Notes

Reaction equation

HRID 439863 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]2[C:6]([CH2:7][C:8]3[NH:9][C:10]4[C:15]([C:16]=32)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:5][CH:4]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:18]=[C:17]2[C:6]([CH2:7][C@@H:8]3[C@H:16]2[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9]3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22408540HCID 22408540, compound

Product 1

HCID 54539506HCID 54539506, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,6-Dihydro-9-methoxyindeno[2,1-b]indole (0.56 g), as a suspension in glacial acetic acid (25 cm3) at 16° C., was treated with sodium cyanoborohydride (1.0 g) in small portions over 6 hours. The resulting solution was stirred for a further 1 hour, and then poured into ice-water (100 cm3). The solution was separated from a small amount of resinous material and the filtrate treated with sodium carbonate (2.5 g) in small portions with vigorous stirring. The colourless solid which separated was collected and crystallised form ethanol as needles. Yield: 0.31 g, 55% M.p. 129°-130° C. 1H NMR (CDCl3) δ: 3.06 (1H, dd, J=16.5 and 1.5 Hz), 3.2-3.8 (1H, br.s), 3.31 (1H, dd, J=16.5 and 6.0 Hz), 3.76 (3H, s), 4.71 (1H, d, J=8.0 Hz), 4.80 (1H, ddd, J=8.0, 6.0 and 2.0 Hz), 6.5 (1H, d, J=8.5 Hz), 6.58 (1H, dd, J=8.5 and 2.5 Hz), 6.99 (1H, d, J=2.5 Hz), 7.15-7.24 (3H, m), 7.33-7.36 (1H, m).

Workup

  1. customThe solution was separated from a small amount of resinous material
  2. additionthe filtrate treated with sodium carbonate (2.5 g) in small portions with vigorous stirring
  3. customThe colourless solid which separated
  4. customwas collected
  5. customcrystallised
  6. customform ethanol as needles

Sources & evidence

ORD record
ord-d7b1aeb2e9504dbab513cd01fbc7785e
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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