Ethanol → Ethyl 3-(cyclopentylamino)-2-hydroxy-2-methylpropanoate

HRID 1880912Notes

Reaction equation

HRID 1880912 reaction equation
[CH3:1][C:2]1([C:5]([O:7][CH3:8])=[O:6])[O:4][CH2:3]1.[CH:9]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:15](O)C>>[CH:9]1([NH:14][CH2:3][C:2]([OH:4])([CH3:1])[C:5]([O:7][CH2:8][CH3:15])=[O:6])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 702EthanolHCID 2906CyclopentylamineHCID 3525005Methyl 2-methylglycidate

Product 1

HCID 57955584Ethyl 3-(cyclopentylamino)-2-hydroxy-2-methylpropanoate

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-methylglycidate (3.18 g, 27 mmol) and cyclopentylamine (4 mL, 41 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 (3.9 g, 60%). [M+H] calc'd for C11H21NO3, 216; found 216.

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 (3.9 g, 60%)

Sources & evidence

ORD record
ord-79d8aeff0d07427b9c2a5907fa94c044
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

Loading…