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

HRID 914141Notes

Reaction equation

HRID 914141 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-5e9efaa13d2e420ab110b15db2c8d8ed
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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