Diethylaluminum chloride → HCID 15512823、化合物

HRID 1633577ノート

反応式

HRID 1633577 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

HCID 15512823HCID 15512823、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-60eda6d834294deb853acf93e41822f9
出典データセット
uspto-grants-2003_01
特許番号
US06503928B2

反応ノート

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