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

HRID 964744

Reaction equation

HRID 964744 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4fa4c0bbcca5428e8b86d0fc10417c36
Source dataset
uspto-grants-1998_06
Patent number
US05770731

Linked notes

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