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

HRID 2194352Notes

Reaction equation

HRID 2194352 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
130 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-5fa12628e48240a0bb38eb2dee07a9ae
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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