(+)-Styrene oxide → (R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide

HRID 374536

Reaction equation

HRID 374536 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]1[O:30][C@@H:23]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(O)C>[CH2:1]([N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:16][CH:17]=1)[CH2:22][C@H:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 114705(+)-Styrene oxideHCID 189972424-(Benzylaminoethoxy)-phenylacetamide

Product 1

HCID 10024191(R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamideYield 64.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-[2-(benzylamino)ethoxy]phenylacetamide (OLS 2135678) (14.0 g), (R)-styrene oxide (5.92 g) and propan-2-ol (200 ml) was heated under reflux for 72 hours. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was purified by dry, flash column chromatography. Elution with 10% methanol in dichloromethane gave (R)-4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide as an oil (12.9 g). This reaction may also be performed in t-amyl alcohol under reflux.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified
  6. customby dry
  7. washElution with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-9371fd0d782c4642815e70f2e160414e
Source dataset
uspto-grants-1996_01
Patent number
US05480910

Linked notes

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