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

HRID 964744

반응식

HRID 964744 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4fa4c0bbcca5428e8b86d0fc10417c36
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770731

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