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

HRID 964744

反応式

HRID 964744 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4fa4c0bbcca5428e8b86d0fc10417c36
出典データセット
uspto-grants-1998_06
特許番号
US05770731

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