Ethanol → Ethyl 2-((cyclopentylamino)methyl)-2-hydroxybutanoate

HRID 1880932Notes

Reaction equation

HRID 1880932 reaction equation
[CH2:1]([C:3]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][O:4]1)[CH3:2].[CH:10]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11]1.[CH2:16](O)C>>[CH:10]1([NH:15][CH2:5][C:3]([OH:4])([CH2:1][CH3:2])[C:6]([O:8][CH2:9][CH3:16])=[O:7])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 702EthanolHCID 2906CyclopentylamineHCID 57955599Methyl 2-ethyloxirane-2-carboxylate

Product 1

HCID 57955553Ethyl 2-((cyclopentylamino)methyl)-2-hydroxybutanoate

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-ethyloxirane-2-carboxylate (1.9 g, 15 mmol) and cyclopentylamine (2.2 mL, 22 mmol) in ethanol (50 mL) was heated at 80° C. for 3 d. The reaction mixture was then concentrated, diluted to EtOAc, washed by NaHCO3, brine and water. Organic layer was dried, concentrated to give a residue which is used for next step without further purification (2.7 g, 80%). [M+H] calc'd for C12H23NO3, 230; found 230.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted to EtOAc
  3. washwashed by NaHCO3, brine and water
  4. customOrganic layer was dried
  5. concentrationconcentrated
  6. customto give a residue which
  7. customis used for next step without further purification (2.7 g, 80%)

Sources & evidence

ORD record
ord-7aa4d6dc42fa4c54a4997808be9e692b
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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