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

HRID 644734노트

반응식

HRID 644734 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-65322071637a4902afa7c0362b7d491e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700599B2

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