Benzylethanolamine → (R)-(-)-5-((Benzyl(2-hydroxyethyl)amino)methyl)pyrrolidin-2-one

HRID 2194352노트

반응식

HRID 2194352 반응식
[O:1]=[C:2]1[NH:6][C@@H:5]([CH2:7]OS(C)(=O)=O)[CH2:4][CH2:3]1.[CH2:13]([NH:20][CH2:21][CH2:22][OH:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([N:20]([CH2:7][C@@H:5]1[NH:6][C:2](=[O:1])[CH2:3][CH2:4]1)[CH2:21][CH2:22][OH:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

3

반응물 2

HCID 4348BenzylethanolamineHCID 13306709(R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonate

생성물 1

HCID 66865389(R)-(-)-5-((Benzyl(2-hydroxyethyl)amino)methyl)pyrrolidin-2-one수율 98.3%

반응 조건

온도
130 °C

실험 절차

A mixture of (−)-methanesulfonic acid (R)-5-oxo-pyrrolidin-2-ylmethyl ester (10.53 g, 54.5 mmol) and 2-(benzylamino)ethanol (32.58 g, 215.5 mmol) was heated at 130° C. in a microwave oven (Personal Chemistry Emrys™ Optimizer) for 45 minutes. The residue was partitioned between water and DCM, the organic phase was washed with brine, dried (Na2SO4) and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH 95/5 respectively) to afford the title compound as yellow oil (13.3 g, 98% yield).

후처리

  1. customThe residue was partitioned between water and DCM
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated under vacuum
  5. customThe crude was purified by flash chromatography (DCM/MeOH 95/5 respectively)

출처 및 근거

ORD 기록
ord-5fa12628e48240a0bb38eb2dee07a9ae
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334286B2

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