Water → 2-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine

HRID 2169176노트

반응식

HRID 2169176 반응식
[C:1]1([CH:7]([NH:9][CH2:10][CH2:11][OH:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>ClCCl>[Si:22]([O:12][CH2:11][CH2:10][NH:9][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 149092-((1-Phenylethyl)amino)ethan-1-olHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

생성물 1

HCID 867258282-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine수율 81.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-(1-phenylethylamino)ethanol (33) (2.71 g, 16.4 mmol, Eq: 1.00) in dichloromethane (60 ml) were added diisopropylethylamine (2.97 g, 4.01 ml, 23.0 mmol, Eq: 1.4) followed by tert-butyldimethylsilyl chloride (2.72 g, 18.0 mmol, Eq: 1.1) at room temperature under nitrogen atmosphere. The resulting solution was stirred for 16 hrs and then it was poured into water (200 ml). The organic layer was separated, washed with brine, and dried with MgSO4, concentrated, and chromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane) to obtain 2-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine (34) (oil, 3.75 g, 13.4 mmol, 81.8% yield).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customchromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-68ba7c02297f4ab081eed934bc364fd6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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