Acetic Acid → Benzyl 4-((cyclopropylamino)methyl)piperidine-1-carboxylate

HRID 220838노트

반응식

HRID 220838 반응식
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O)(=O)C.[CH2:9]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[CH2:21][CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([BH3-])#N.[Na+]>CO>[CH2:9]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH:4][CH:1]2[CH2:3][CH2:2]2)[CH2:21][CH2:20]1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 2776272Benzyl 4-formylpiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 57555432Benzyl 4-((cyclopropylamino)methyl)piperidine-1-carboxylate수율 47%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Cyclopropylamine (1.4 g, 24.4 mmol) and acetic acid (0.5 ml) were added to a solution of 4-formyl-piperidine-1-carboxylic acid benzyl ester from Example E33.2 (5.5 g, 22.2 mmol) in methanol (49.5 ml) and the mixture was stirred for 1 h at room temperature. Sodium cyanoborohydride (1.84 g, 28.9 mmol) was added and the mixture was stirred for 20 h at room temperature under an inert atmosphere. Solvents were removed in vacuo and azeotroped with toluene. The residue was dissolved in EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% dichloromethane) to yield the title compound (3.0 g, 47%).

후처리

  1. stirringthe mixture was stirred for 20 h at room temperature under an inert atmosphere
  2. customSolvents were removed in vacuo
  3. customazeotroped with toluene
  4. dissolutionThe residue was dissolved in EtOAC
  5. washwashed with saturated NaHCO3
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% dichloromethane)

출처 및 근거

ORD 기록
ord-30e1b01a1f9340e798e77cc3cde53b73
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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