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

HRID 612813노트

반응식

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

생성물 1

HCID 100671724-(((Tert-butyldiphenylsilyl)oxy)methyl)aniline수율 91.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c516b40f876e4e7c93b23337f994576a
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06005002

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