2-(Methylamino)ethanol → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

HRID 572789

반응식

HRID 572789 반응식
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Si:17]([O:5][CH2:4][CH2:3][NH:2][CH3:1])([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

생성물 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamine수율 53%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

To a solution of 2-(methylamino)ethanol (2.14 mL, 26.6 mmol) in DCM (60 mL) was added triethylamine (4.1 mL, 29.3 mmol),N,N-dimethylpyridin-4-amine (1.63 g, 13.3 mmol) and tert-butylchlorodiphenylsilane (7.6 mL, 29.3 mmol). The reaction was stirred overnight at 40° C. After cooling to RT, the reaction was quenched with water (20 mL) and ether (100 mL). The organic phase was washed with water, brine, dried over magnesium sulfate and concentrated to afford the crude product which was purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM. The solvent was evaporated to dryness to afford 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine (4.4 g, 53%) as a colorless oil. NMR Spectrum (DMSOd6): 0.99 (s, 9H), 2.27 (s, 3H), 2.63 (t, 2H), 3.68 (t, 2H), 7.40-7.49 (m, 6H), 7.60-7.65 (m, 4H).

후처리

  1. temperatureAfter cooling to RT
  2. customthe reaction was quenched with water (20 mL) and ether (100 mL)
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM
  8. customThe solvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-fda01a43cee343629498adfbe2f2e243
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029374B2

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