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

HRID 914151Notes

Reaction equation

HRID 914151 reaction equation
[CH3:1][C:2]1([C:5]([O:7][CH3:8])=[O:6])[O:4][CH2:3]1.[CH:9]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:16](O)C>>[CH:9]1([NH:15][CH2:3][C:2]([OH:4])([CH3:1])[C:5]([O:7][CH2:8][CH3:16])=[O:6])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 702EthanolHCID 7965CyclohexylamineHCID 3525005Methyl 2-methylglycidate

Product 1

HCID 57955527Ethyl 3-(cyclohexylamino)-2-hydroxy-2-methylpropanoate

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-methylglycidate (3.2 mL, 30 mmol) and cyclohexylamine (5.2 mL, 45 mmol) in ethanol (50 mL) was heated at 80° C. for 24 h. 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 (6.7 g, 97%). [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 (6.7 g, 97%)

Sources & evidence

ORD record
ord-b459b161421242f8bbc65eaf48388c5f
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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