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

HRID 2194352ノート

反応式

HRID 2194352 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
130 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5fa12628e48240a0bb38eb2dee07a9ae
出典データセット
uspto-grants-2012_12
特許番号
US08334286B2

反応ノート

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