Hydrochloric Acid → (4-Benzylmorpholin-2-yl)(cyclopropyl)methanol

HRID 30322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30322
B.C1COCC1.[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH:20]([CH:22]2[CH2:24][CH2:23]2)[OH:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.CO>[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH:20]([CH:22]2[CH2:24][CH2:23]2)[OH:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 597892904-Benzyl-2-(cyclopropyl(hydroxy)methyl)morpholin-3-one

Produkt 1

HCID 59789293(4-Benzylmorpholin-2-yl)(cyclopropyl)methanolAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Borane-THF complex (1M solution in THF, 30 mL, 30 mmol, 4.1 eq) is added slowly to a solution of 75 (1.9 g, 7.3 mmol) in THF (100 mL). The reaction is heated to 60° C. After 24 hours MeOH and hydrochloric acid (2M, excess) are added and the resulting mixture heated for one hour at the same temperature. After careful addition of saturated NaHCO3 solution and EtOAc the aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried over magnesium sulphate and the solvent is removed in vacuo. Purification by ion exchange chromatography gives 76 (1.1 g, 61%). MW 247.34; C15H21NO2; LCMS (6 min method) m/z 248 [M+H]+, RT 2.48 min

Aufarbeitung

  1. temperaturethe resulting mixture heated for one hour at the same temperature
  2. extractionis extracted with EtOAc
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is removed in vacuo
  6. customPurification by ion exchange chromatography

Quellen und Nachweise

ORD-Eintrag
ord-48cfe3673d67467abfa9814c6d2feaf2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423037B2

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