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Cyclopentanone → Methyl1-[(cyclopentylamino)methyl]cyclopentane-1-carboxylate

HRID 2234511
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HRID 2234511 반응식
[CH3:1][O:2][C:3]([C:5]1([CH2:10][NH2:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[C:12]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:10][NH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:4]
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참가 물질

6

반응물 4

HCID 8452CyclopentanoneHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 13285792Methyl 1-(aminomethyl)cyclopentanecarboxylate2회

생성물 1

HCID 68683992Methyl1-[(cyclopentylamino)methyl]cyclopentane-1-carboxylate수율 81%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

Methyl1-(aminomethyl)cyclopentane-1-carboxylate (Intermediate 259; 1.5 g, 9.54 mmol) and cyclopentanone (1.0 mL, 11.45 mmol) were stirred in DCM (40 mL). Sodium acetate (940 mg, 11.45 mmol) and sodium triacetoxyborohydride (3.04 g, 14.31 mmol) were added. The mixture was stirred at room temperature for 48 hours. The reaction mixture was filtered and the filtrate concentrated. The residue was dissolved in methanol and absorbed on to an SCX column, which was then washed with methanol and eluted with ammonia in methanol. Product containing fractions were combined and evaporated to yield the title compound as a colourless oil (1.64 g, 81%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue was dissolved in methanol
  4. customabsorbed on to an SCX column, which
  5. washwas then washed with methanol
  6. washeluted with ammonia in methanol
  7. additionProduct containing fractions
  8. customevaporated

출처 및 근거

ORD 기록
ord-e9f0274a85684172b27426ecfdf37dd0
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709471B2

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