Sodium borohydride → HCID 13604465, Verbindung

HRID 2418736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2418736
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH:14]([OH:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 13243522HCID 13243522, Verbindung

Produkt 1

HCID 13604465HCID 13604465, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,5-dione (0.14 g) and sodium borohydride (7 mg) in ethanol (10 ml) was stirred at room temperature for 18 hours. The ethanol was removed under reduced pressure, and the residue dissolved in dichloromethane (25 ml). The solution was extracted with 2N HCl (2×20 ml) and saturated brine (20 ml), and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue triturated with ether to give 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-5-hydroxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, mp 167°-169.5° C., [α]D =-193° (c=0.52 in DMF). The substance was also obtained by hydrogenation of the benzazepin-2,5-dione derivative with H2 /Pt in ethanol.

Aufarbeitung

  1. customThe ethanol was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane (25 ml)
  3. extractionThe solution was extracted with 2N HCl (2×20 ml) and saturated brine (20 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-8c04a579b64c455d931579f559da52f8
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04473575

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