Dichloromethane → HCID 59295122, Verbindung

HRID 2233001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233001
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH:16]3[CH:13]([CH2:14][C:15]3=[O:18])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)Cl.[BH4-].[Na+]>CCO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:17][C@H:16]3[C@H:13]([CH2:14][C@H:15]3[OH:18])[CH2:12]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 218925103-Tosyl-3-azabicyclo[3.2.0]heptan-6-one

Produkt 1

HCID 59295122HCID 59295122, VerbindungAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 3-[(4-methylphenyl)sulfonyl]-3-azabicyclo[3.2.0]heptan-6-one (120 mg, 0.45 mmol) in EtOH:DCM (6 mL, 5:1) at 0° C. was added NaBH4 (21 mg, 0.54 mmol) portion-wise. After stirring at 25° C. for 0.5 hr, the solution was concentrated and then partitioned between DCM and water. The aqueous layer was extracted several times with DCM. The organic fractions were combined, concentrated and purified by column chromatography (silica, 0-0.5% MeOH in DCM (0.5% NH4OH)) affording the title compound as a white solid (109 mg, 90%): LC/MS (ES) m/e 268 (M+H)+.

Aufarbeitung

  1. concentrationthe solution was concentrated
  2. custompartitioned between DCM and water
  3. extractionThe aqueous layer was extracted several times with DCM
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica, 0-0.5% MeOH in DCM (0.5% NH4OH))

Quellen und Nachweise

ORD-Eintrag
ord-687a730327a34036b8cf50adc73351bf
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709472B2

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