Sodium Hydroxide → HCID 15082735, compound

HRID 439838Notes

Reaction equation

HRID 439838 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[C:12]4[C:17]([CH2:18][C:6]=3[C:5]=2[CH:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C@@H:7]3[C:12]4[C:17]([CH2:18][C@@H:6]3[C:5]=2[CH:4]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 15082721HCID 15082721, compound

Product 1

HCID 15082735HCID 15082735, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,10-Dihydro-8-methoxyindeno[1,2-b]indole (770 mg, 3.3 mmol) was reacted with sodium cyanoborohydride (1.0 g, 16 mmol), in glacial acetic acid (17 cm3) solution. After 30 minutes, the solution was poured into ice/water, stirred for 1 hour, and neutralised with sodium hydroxide. The colourless reaction mixture was extracted into diethylether, the organic layers, dried (Na2SO4), and concentrated in vacuo. The residue was column chromatographed (10% ethyl acetate/petrol 60°-80° C.) to yield the title compound as a colourless solid. Yield: 520 mg (66%). M.p. 101° C. 1H NMR (CDCl3) δ: 3.28 (1H, dd,), 3.57 (1H, dd,), 3.80 (3H, s,), 3.85 (1H, br,), 4.24 (1H, dd,), 5.30 (1H, d,), 6.6-7.4 (7H, m,).

Workup

  1. extractionThe colourless reaction mixture was extracted into diethylether
  2. dry with materialthe organic layers, dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customchromatographed (10% ethyl acetate/petrol 60°-80° C.)

Sources & evidence

ORD record
ord-ae18a2b3bdf74641b9c9a258f303d4cd
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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