Sodium borohydride → 543713-48-0

HRID 2111676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111676
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1)=O)C>C(O)C>[OH:5][CH2:6][C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 10588096Ethyl 5-(aminomethyl)isoxazole-3-carboxylate, 5-BOC protected

Produkt 1

HCID 67284568543713-48-0Ausbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (610 mg, 16 mmol) was added in portions to a solution of 3-ethoxycarbonyl-5-[N-(tert-butyloxycarbonyl)aminomethyl]isoxazole (Method 73; 1.62 g, 6 mmol) in ethanol (15 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 4 hours then quenched with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with EtOAc and the organics washed with brine then dried (MgSO4). The solvent was removed by evaporation to give the title compound (1.25 g, 91%). NMR (DMSO): 1.38 (s, 9H), 4.21 (d, 2H), 4.44 (s, 2H), 5.40 (br s, 1H), 6.21 (s, 1H), 7.49 (br s, 1H); m/z 229 (MH)+.

Aufarbeitung

  1. customthen quenched with saturated aqueous sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organics washed with brine
  4. dry with materialthen dried (MgSO4)
  5. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-07fe8723aa004bea94974bd30ed18511
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521453B2

Notizen zur Reaktion

Wird geladen…