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2,4-Dimethoxybenzaldehyde → Isohexane ethyl acetate

HRID 1183015
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HRID 1183015 반응식
[NH2:1][CH:2]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]2)=[CH:10][CH:9]=1)[C:3]#[N:4].[CH3:23][O:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:26]=1[CH:27]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:15][CH2:16][O:17][C:18]([CH3:21])=[O:19].[CH3:5][CH2:6][CH2:7][CH:8]([CH3:13])[CH3:9].[CH3:23][O:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:26]=1[CH2:27][NH:1][CH:2]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]2)=[CH:10][CH:9]=1)[C:3]#[N:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 691752,4-DimethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 66917020HCID 66917020, 화합물2회

생성물 2

HCID 21882781Isohexane ethyl acetateHCID 669170122-(2,4-Dimethoxy-benzylamino)-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-amino-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile (Intermediate B) (480 mg, 1.6 mmol) in DCM (13 mL) is added 2,4-dimethoxybenzaldehyde (319 mg, 1.92 mmol) and sodium triacetoxyborohydride (529 mg, 2.49 mmol) and the reaction is stirred at RT for 15 h. After this time saturated aqueous sodium hydrogen carbonate solution (20 mL) is added and the reaction is stirred at RT for 0.5 h. DCM (20 mL) is added and the layers are separated. The organic phase is washed with brine (20 mL) then dried over Na2SO4 and the solvent is removed in vacuo. Chromatography (SiO2, EtOAc:iso-hexane 2:3) affords the title compound as a colourless oil.

후처리

  1. stirringthe reaction is stirred at RT for 0.5 h
  2. customthe layers are separated
  3. washThe organic phase is washed with brine (20 mL)
  4. dry with materialthen dried over Na2SO4
  5. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-2a04d8b7598b40238b7a8fc2ee51593d
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08664228B2

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