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

HRID 612813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612813
[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].[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 223AmmoniumHCID 15528110(4-Nitro-benzyl) t-butyl-di-phenyl-silyl ether

Produkt 1

HCID 100671724-(((Tert-butyldiphenylsilyl)oxy)methyl)anilineAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2a (5.00 g, 12.80 mmol) in ethanol (100 mL) was added Pd/C 10%(1.50 g) and ammonium fornate (4.60 g) in one portion at 20° C. After 1.5 h the catalyst was removed by filtration, the filtrate concentrated under vacuum and the residue partitioned between EtOAc:H2O. The organic layer was dried (MgSO4) and concentrated to give 3a as an oil yield: 4.24 g (91%) νmax /cm-1 (film): 3433, 3378 (NH2), 2931, 2857 (CH2, asym. sym.): 1H-NMR, δH : 1.00 (s, 9H. t-Bu), 4.57 (s, 2H. CH2), 4.98 (s broad, 2H, NH2), 6.52 (d, 2H, J=8.25 Hz, Harom3+5), 6.96 (d, 2H, Harom2+6), 7.42-7.46 (m, 5H, Ph), 7.62-7.65 (m, 5H, Ph): MS, (EI), (361.56); m/z: 361 (M+, 8), 304 (M-t-Bu, 100), 199 (Ph2SiOH+, 100); anal (C23H27NOSi), C, H, N.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c516b40f876e4e7c93b23337f994576a
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005002

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