Diethylaluminum chloride → HCID 15512823, 화합물

HRID 1633577노트

반응식

HRID 1633577 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.[CH3:16][N:17]([CH:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:26](O)=[O:27])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].CC[Al](Cl)CC.C1C=CC2N(O)N=NC=2C=1.C[N+]1([O-])CCOCC1>CN(C)C=O.O.CCOC(C)=O>[C:21]([O:20][C:18](=[O:19])[N:17]([C@H:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:26]([N:11]1[CH2:12][CH2:13][CH:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:14][CH3:15])[CH2:9][CH2:10]1)=[O:27])[CH3:16])([CH3:24])([CH3:22])[CH3:23]

참가 물질

9

반응물 5

HCID 7277Diethylaluminum chlorideHCID 757711-HydroxybenzotriazoleHCID 82029Methyl morpholine oxideHCID 52406092-{[(Tert-butoxy)carbonyl](methyl)amino}-3-phenylpropanoic acidHCID 155128224-(5-Fluoro-2-methoxyphenyl)piperidine

생성물 1

HCID 15512823HCID 15512823, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

The above product of 4-(5-fluoro-2-methoxy-phenyl)-piperidine was dissolved in N,N-dimethylformamide (10 mL) at 0° C. To the resulting solution, 0.70 g (2.5 mmole) of 2-[N-methyl-N-(tert-butoxycarbonyl)-amino]-3-phenyl-propionic acid in a minimal amount of DMF was added, followed by DEAC (0.48 g, 2.5 mmole), HOBT (0.41 g, 2.5 mmole) and NMO (0.37 mL, 3.4 mmole) and the mixture was stirred overnight (the reaction temperature was slowly allowed to warm up to room temperature). The reaction mixture was diluted with water (50 mL) and EtOAc (50 mL) and the layers separated. The aqueous layer was washed with HCl (1 N), saturated NaHCO3, and the combined aqueous layers were extracted three times with EtOAc. The combined organic layers were dried over NA2SO4 and concentrated. Flash chromatography, gradient elution with 1:4 EtOAc-hexane to 3:7 EtOAc-hexane to afford (R)-{1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-piperidin-1-yl]-2-oxo-ethyl}-methyl-carbamic acid tert-butyl ester as a yellow oil.

후처리

  1. customthe layers separated
  2. washThe aqueous layer was washed with HCl (1 N), saturated NaHCO3
  3. extractionthe combined aqueous layers were extracted three times with EtOAc
  4. customThe combined organic layers were dried over NA2SO4
  5. concentrationconcentrated
  6. washFlash chromatography, gradient elution with 1:4 EtOAc-hexane to 3:7 EtOAc-hexane

출처 및 근거

ORD 기록
ord-60eda6d834294deb853acf93e41822f9
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06503928B2

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