3,3-Dimethylbutanal → 4-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic Acid Methyl Ester

HRID 220844노트

반응식

HRID 220844 반응식
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.Cl.Cl.[CH3:10][O:11][C:12](=[O:29])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[C:15]([CH3:28])[CH:14]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:10][O:11][C:12](=[O:29])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:4][CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1])[CH2:24][CH2:23]2)=[C:15]([CH3:28])[CH:14]=1

참가 물질

5

반응물 3

HCID 763353,3-DimethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 670538063-Methyl-4-(2-piperazin-1-yl-ethoxy)-benzoic Acid Methyl Ester Dihydrochloride

생성물 1

HCID 575552114-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic Acid Methyl Ester수율 34%

시약·촉매·용매 1

HCID 10129899Acetic acid methanol용매

실험 절차

3,3-Dimethylbutyraldehyde (54 mg, 0.53 mmol) was added to a solution of 3-methyl-4-(2-piperazin-1-yl-ethoxy)-benzoic acid methyl ester dihydrochloride from Example E40.2 (146 mg, 0.42 mmol) in methanol/acetic acid (99:1, v/v, 10 ml) and the mixture was stirred at room temperature for 1 h. Sodium cyanoborohydride (42 mg, 0.69 mmol) was added, and the mixture was stirred at room temperature for 18 h then concentrated in vacuo. The residue was dissolved in EtOAc, washed with saturated NaHCO3, water then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; EtOAc) to yield the title compound (64 mg, 34%).

후처리

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3, water
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; EtOAc)

출처 및 근거

ORD 기록
ord-ec7264c6e02a429682a23e3cc7306a2b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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