Benzylethanolamine → HCID 46221964, compound

HRID 2194347Notes

Reaction equation

HRID 2194347 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 13306708(S)-(5-Oxopyrrolidin-2-yl)methyl methanesulfonate

Product 1

HCID 46221964HCID 46221964, compoundYield 96.4%

Conditions

Temperature
130 °C

Procedure

A mixture of (+)-methanesulfonic acid (S)-5-oxo-pyrrolidin-2-ylmethyl ester (500 mg, 2.59 mmol) and 2-(benzylamino)ethanol (1.56 g, 10.36 mmol) was heated at 130° C. in a microwave oven (Personal Chemistry Emrys™ Optimizer) for 40 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 from 95/5 to 90/10 respectively) to afford the title compound as yellow oil (620 mg, 96% 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 from 95/5 to 90/10 respectively)

Sources & evidence

ORD record
ord-82cfdc70edf0478893468d61a6549479
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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