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

HRID 220844ノート

反応式

HRID 220844 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 10129899Acetic acid methanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ec7264c6e02a429682a23e3cc7306a2b
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

反応ノート

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