Imidazole → 2-(tert-butyldiphenylsilyloxy)-N-ethylethanamine

HRID 1771172노트

반응식

HRID 1771172 반응식
N1C=CN=C1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[CH2:24]([NH:26][CH2:27][CH2:28][OH:29])[CH3:25]>C(Cl)Cl>[Si:10]([O:29][CH2:28][CH2:27][NH:26][CH2:24][CH3:25])([C:6]([CH3:9])([CH3:8])[CH3:7])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 80722-(Ethylamino)ethanolHCID 94078tert-Butyldiphenylchlorosilane

생성물 1

HCID 580801592-(tert-butyldiphenylsilyloxy)-N-ethylethanamine수율 80.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

Imidazole (1.53 g, 22.44 mmol) and a solution of tert-butylchlorodiphenylsilane (4.63 g, 16.83 mmol) in DCM (10 ml) were added sequentially to a solution of 2-(ethylamino)ethanol (1.099 ml, 11.22 mmol) in DCM (30 ml) and the resulting reaction mixture was stirred at room temperature overnight. The mixture was diluted with DCM and washed with 1N aq. NaHSO4 and saturated aq. NaHCO3. The organic layer was dried (Na2SO4), concentrated under reduced pressure to give a residue which was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes) to provide the title compound (2.95 g, yield: 80%).

후처리

  1. customthe resulting reaction mixture
  2. washwashed with 1N aq. NaHSO4 and saturated aq. NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-d05dbf30b2df427d893d81ff40dd24cc
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09248140B2

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