Cyclooctanecarbaldehyde → N-[9-(cyclooctylmethyl)-9-azabicyclo[3.3.1]nonan-3-yl]xanthene-9-carboxamide

HRID 370272

Reaction equation

HRID 370272 reaction equation
Cl.[CH:2]12[NH:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH2:5][CH:4]([NH:11][C:12]([CH:14]1[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:21][C:20]3[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH2:3]2.[CH:28]1([CH:36]=O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO>[CH:28]1([CH2:36][N:10]2[CH:6]3[CH2:7][CH2:8][CH2:9][CH:2]2[CH2:3][CH:4]([NH:11][C:12]([CH:14]2[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:21][C:20]4[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=4)=[O:13])[CH2:5]3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 81190CyclooctanecarbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23283000N-(9-azabicyclo[3.3.1]nonan-3-yl)xanthene-9-carboxamide hydrochloride

Product 1

HCID 15480669N-[9-(cyclooctylmethyl)-9-azabicyclo[3.3.1]nonan-3-yl]xanthene-9-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

38.5 mg of N-(9-azabicyclo[3.3.1]nonan-3-yl)xanthene-9-carboxamide hydrochloride and 44.1 mg of cyclooctanecarbaldehyde were suspended in 3 ml of methanol at room temperature, and 1.60 g of sodium triacetoxyborohydride was added thereto, followed by stirring for 12 hours at the same temperature. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the obtained residue was purified by preparative thin layer chromatography (Kieselgel™60F254, Art5744 produced by Merck Co.: chloroform/methanol=19/1), and 9.0 mg of the title compound as a white solid was obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by preparative thin layer chromatography (Kieselgel™60F254, Art5744 produced by Merck Co.: chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-579a5cdcf625477db273cebaf834e15b
Source dataset
uspto-grants-2000_10
Patent number
US06140338

Linked notes

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