Sodium Hydroxide → (+/-)-2-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-2,3,4,9-tetrahydro-1-H-beta-carboline

HRID 1987768Notes

Reaction equation

HRID 1987768 reaction equation
[CH3:1][C:2]1([CH:17]=O)[CH2:6][CH:5]2[CH:7]([CH3:16])[C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:12])[C:10]([CH3:11])=[C:4]2[O:3]1.[CH2:19]1[C:31]2[NH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH2:22][CH2:21][NH:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[N+:13]([C:8]1[CH:7]([CH3:16])[CH:5]2[CH2:6][C:2]([CH2:17][N:20]3[CH2:21][CH2:22][C:23]4[C:24]5[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=5)[NH:30][C:31]=4[CH2:19]3)([CH3:1])[O:3][C:4]2=[C:10]([CH3:11])[C:9]=1[CH3:12])([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 107838Tetrahydro-beta-carbolineHCID 5049666Sodium triacetoxyborohydrideHCID 866073542,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-aldehyde

Product 1

HCID 86608812(+/-)-2-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-2,3,4,9-tetrahydro-1-H-beta-carbolineYield 45.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2.0 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-aldehyde, 1.52 g of 2,3,4,9-tetrahydro-1H-beta-carboline, 50 ml of methylene chloride, 0.8 ml of acetic acid and 2.04 g of sodium triacetoxyborohydride were added, followed by stirring overnight at room temperature. The mixture was poured into ice-water and an aqueous sodium hydroxide solution was added. The reaction solution was extracted with chloroform, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:ethyl acetate=50:1) to obtain 1.49 g of the objective product.

Workup

  1. extractionThe reaction solution was extracted with chloroform
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationafter the solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-381307a8ba9d4afeb6a1c6e06e47a99c
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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