HCID 59598472, Verbindung → (R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate

HRID 2266273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266273
CON(C)[C:4]([C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].[CH3:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][Mg]Cl>C1COCC1>[CH3:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:4]([C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:7]1)=[O:5]

Komponenten

4

Edukt 2

HCID 59598472HCID 59598472, VerbindungHCID 178495008HCID 178495008, Verbindung

Produkt 1

HCID 59598474(R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (1.37 g, 5.0 mmol) in THF (10 mL) at −20° C., there was added (4-methoxybutyl)magnesium chloride in THF (1.47 M, 10.2 mL, 15.0 mmol) dropwise such that the temperature remained below −20° C. After addition, the resulting solution was warmed to rt, and quenched with 1 N aq HCl (10 mL). The organic layer was separated, and the aqueous layer was extracted with ether (3×5 mL). The combined organic layers were washed with satd aq NaHCO3 (10 mL) and brine (5 mL), and dried over Na2SO4. The solvent was then removed in vacuo to give (R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate (1.41 g, 93%), which was used for the next step without purification; MS m/s 324 (M+Na+).

Aufarbeitung

  1. customremained below −20° C
  2. additionAfter addition
  3. customquenched with 1 N aq HCl (10 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ether (3×5 mL)
  6. washThe combined organic layers were washed with satd aq NaHCO3 (10 mL) and brine (5 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was then removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ff5c9f563aa64c0c9fe1a2dd467a80b7
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858624B2

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