Sodium Bicarbonate → 1,1-Dimethylethyl (2S)-4-[(6-amino-4-methyl-3-pyridinyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 644749노트

반응식

HRID 644749 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[C:4]([CH3:10])[CH:3]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:16]2[CH2:15][CH2:14][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:12]([CH3:11])[CH2:17]2)=[C:4]([CH3:10])[CH:3]=1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 552846706-Amino-4-methylnicotinaldehyde

생성물 1

HCID 592621751,1-Dimethylethyl (2S)-4-[(6-amino-4-methyl-3-pyridinyl)methyl]-2-methyl-1-piperazinecarboxylate수율 53.6%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A mixture of 6-amino-4-methyl-3-pyridinecarbaldehyde (D99) (0.053 g, 0.39 mmol), 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (0.117 g, 0.58 mmol) and sodium tri(acetoxy)borohydride (0.206 g, 0.97 mmol) in 1,2-DCE (10 mL) was sonicated to aid dissolution of the starting material then stirred at room temperature overnight. Saturated aqueous NaHCO3 (30 mL) was added and the mixture was stirred for 24 h. The reaction mixture was extracted with DCM (3×10 mL) and the organics were dried and concentrated to give the crude title compound as an oil (0.067 g) which was used in the next step without further purification. MS (ES): MH+ 321.3, MNa+ 343.3.

후처리

  1. customwas sonicated
  2. dissolutiondissolution of the starting material
  3. stirringthe mixture was stirred for 24 h
  4. extractionThe reaction mixture was extracted with DCM (3×10 mL)
  5. customthe organics were dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dede3eaa4a914d8abb62d2be7be2d646
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700599B2

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