Ammonium formate → 4-(((Tert-butyldiphenylsilyl)oxy)methyl)aniline

HRID 964744

Reaktionsgleichung

Reaktionsgleichung von HRID 964744
[C:1]([Si:5]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([Si:5]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 15528110(4-Nitro-benzyl) t-butyl-di-phenyl-silyl ether

Produkt 1

HCID 100671724-(((Tert-butyldiphenylsilyl)oxy)methyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 13 (5.00 g, 12.77 mmol) in ethanol (100 ml) was added Pd/C (10%, 1.50 g) and ammonium formate (4.60 g) at room temperature. After 1.5 h the catalyst was removed by filtration, the filtrate concentrated to dryness under vacuum and the residue partitioned between EtOAc:H2O. The organic layer was dried (MgSO4) and concentrated under vacuum to give 14 as an oil; yield: 4.24 g (92%); vmax /cm-1 (film): 3433, 3378 (NH2), 2931, 2857 (CH2, asym., sym.); 1H-NMR, dH : 1.00 (9H, s, t-Bu), 4.57 (2H, s, CH2), 4.98 (2H, s broad, NH2), 6.52 (2H, d, J=8.25, Harom3+5), 6.96 (2H, d, Harom2+6), 7.42-7.46 (5H, m, Ph), 7.62-7.65 (5H, m, Ph); MS, (EI), (361.56); m/z: 361 (M+, 8), 304 (M - t-Bu, 100), 199 (Ph2SiOH+, 100); C23H27NOSi.

Aufarbeitung

  1. customAfter 1.5 h the catalyst was removed by filtration
  2. concentrationthe filtrate concentrated to dryness under vacuum
  3. customthe residue partitioned between EtOAc
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4fa4c0bbcca5428e8b86d0fc10417c36
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770731

Verknüpfte Notizen

Wird geladen…