(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamide → (S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate

HRID 451767

Reaktionsgleichung

Reaktionsgleichung von HRID 451767
[CH:1]1([CH2:7][C@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:9](N(OC)C)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:23][CH2:24][Mg+].[Br-]>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][C@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:9](=[O:10])[CH2:23][CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 10495486(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamideHCID 178461630HCID 178461630, Verbindung

Produkt 1

HCID 15730499(S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (S)-tert-butyl 3-cyclohexyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (5.23 g, 16.66 mmol) in anhydrous toluene (80 mL) at −20° C. was added EtMgBr (3 M in Et2O, 16.7 mL, 49.97 mmol) slowly. The reaction was allowed to warm to 0° C., and stirred at this temperature for 2 h. The reaction was quenched with 1 M HCl at 0° C. and extracted with EtOAc. The organic phase was washed with sat. aq. NaHCO3, brine, concentrated to give (S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate. The product was used in the next step without further purification. MS ESI +ve m/z 306 (M+Na).

Aufarbeitung

  1. customThe reaction was quenched with 1 M HCl at 0° C.
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with sat. aq. NaHCO3, brine
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-56ff7388ade14b54ab8a34209b8ef806
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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