Sodium Bicarbonate → N-[1-(4-methyl-2-pyridylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

HRID 366417노트

반응식

HRID 366417 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=O)[CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:31])[C:18]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)([OH:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:10]2[CH2:11][CH2:12][CH:13]([NH:16][C:17](=[O:31])[C:18]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)([OH:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH2:15]2)[CH:3]=1

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 100118944-Methylpyridine-2-carbaldehydeHCID 10662143N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide

생성물 1

HCID 23289913N-[1-(4-methyl-2-pyridylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 63651,1-Dichloroethane용매

실험 절차

75 Milligrams of 4-methyl-2-pyridinecarbaldehyde, 58.3 mg of N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide and 12 mg of acetic acid were dissolved in 10 ml of dichloroethane. To the solution 68 mg of sodium triacetoxyborohydride was added at room temperature, followed by an hour's stirring at the same temperature. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution, extracted with chloroform, dried over anhydrous magnesium sulfate and removed of the solvent by reduced pressure distillation. The residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254Art 5744 (Merck), chloroform/methanol=9/1] to give 49.5 mg of the title compound as a white solid.

후처리

  1. waitfollowed by an hour
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customremoved of the solvent by reduced pressure distillation
  5. customThe residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254Art 5744 (Merck), chloroform/methanol=9/1]

출처 및 근거

ORD 기록
ord-e6be6a68ac3f4643b4f05d94da177b6e
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130232

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