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

HRID 370272

반응식

HRID 370272 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-579a5cdcf625477db273cebaf834e15b
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140338

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