Sodium borohydride → HCID 71060241, Verbindung

HRID 1036717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036717
[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][CH2:22][C:10]2([N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:13]=[N:12][C:11]2=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][CH2:22][C:10]2([N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:13][NH:12][C:11]2=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 71060280HCID 71060280, Verbindung

Produkt 1

HCID 71060241HCID 71060241, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-oxo-1-phenyl-1,3,7-triaza-spiro[4.5]dec-2-ene-7-carboxylic acid tert-butyl ester (130 mg, 0.39 mmol) in methanol (3 ml) was added sodium borohydride (22 mg, 0.59 mmol). The reaction mixture was stirred at RT for 1 hour. The reaction mixture was concentrated in vacuo. The residue was dissolved with EtOAc (5 ml) and washed with a saturated solution of sodium bicarbonate (10 ml). The aqueous phase was extracted with further EtOAc (5 ml). The organics portions were combined, dried (MgSO4) and concentrated in vacuo to afford an oil. Purification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved with EtOAc (5 ml)
  3. washwashed with a saturated solution of sodium bicarbonate (10 ml)
  4. extractionThe aqueous phase was extracted with further EtOAc (5 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto afford an oil
  8. customPurification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0bce9d4611a24f6a85146c05a605dacb
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546416B2

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