Sodium Bicarbonate → tert-butyl (2S)-2-methyl-4-[2-methyl-4-(methylamino)benzyl]piperazine-1-carboxylate

HRID 534764ノート

反応式

HRID 534764 の反応式
[CH3:1][C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][C@H:13]1[CH2:18][NH:17][CH2:16][CH2:15][N:14]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH3:1][C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH2:4][N:17]1[CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:13]([CH3:12])[CH2:18]1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 450836492-Methyl-4-(methylamino)benzaldehyde

生成物 1

HCID 59262129tert-butyl (2S)-2-methyl-4-[2-methyl-4-(methylamino)benzyl]piperazine-1-carboxylate収率 37%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a mixture of 2-methyl-4-(methylamino)benzaldehyde (D93) (0.397 g) and 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (0.533 g, 2.66 mmol) in 1,2-DCE (35 mL) was added sodium tri(acetoxy)borohydride (0.847 g, 4.00 mmol) and the reaction stirred at room temperature overnight. Saturated aqueous NaHCO3 (30 mL) was added and the mixture was stirred for 4 h. The reaction mixture was extracted with DCM and the organics were dried and concentrated to give the crude product which was purified by column chromatography. Elution with ether/petroleum ether gave the title compound as a colourless oil (0.328 g).

後処理

  1. stirringthe mixture was stirred for 4 h
  2. extractionThe reaction mixture was extracted with DCM
  3. customthe organics were dried
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography
  7. washElution with ether/petroleum ether

出典と根拠

ORDレコード
ord-14d63a0ce4454544a58db7da5952d504
出典データセット
uspto-grants-2014_10
特許番号
US08853218B2

反応ノート

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