4-Methylmorpholine → HCID 54543994, Verbindung

HRID 1978836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978836
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH: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].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>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][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:14][CH3:15])=[CH:9][CH2:10]1)=[O:27])[CH3:16])([CH3:24])([CH3:22])[CH3:23]

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 52406092-{[(Tert-butoxy)carbonyl](methyl)amino}-3-phenylpropanoic acidHCID 18679661HCID 18679661, Verbindung2×

Produkt 1

HCID 54543994HCID 54543994, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The crude product of 4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine (0.49 g, 2.4 mmole) (Intermediate 9) was dissolved in N,N-dimethylformamide (10 mL) at 0° C., and the resulting solution treated with 2-[N-methyl-N-(tert-butoxycarbonyl)-amino]-3-phenyl-propionic acid (0.73 g, 2.6 mmole) in a minimal amount of DMF, DAEC (0.50 g, 2.6 mmole), HOBT (0.42 g, 3.1 mmole) and NMM (0.40 mL, 3.6 mmole). The mixture was stirred overnight, and was diluted with water (50 mL) and EtOAc (50 mL). The layers were separated and the organic layer was washed with HCl (1N), saturated NaHCO3, and the combined aqueous washings were extracted three times with EtOAc (3×25 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford (R)-{1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-2-oxo-ethyl}-methyl-carbamic acid tert-butyl ester as a yellow oil.

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic layer was washed with HCl (1N), saturated NaHCO3
  3. extractionthe combined aqueous washings were extracted three times with EtOAc (3×25 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a39bf0fb5f224c91879f63bd1076c7b9
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239126B1

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