Isopropanol → Ethyl 3-amino-4-methyl-pent-2-enoate

HRID 324795Notes

Reaction equation

HRID 324795 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[NH4+:5].[CH2:6]1[CH2:11][CH2:10][CH2:9][CH2:8]C1.[OH-:12].[NH4+].[CH:14](O)(C)C>>[NH2:5][C:10]([CH:9]([CH3:8])[CH3:14])=[CH:11][C:6]([O:4][CH2:1][CH3:2])=[O:12]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 8078CyclohexaneHCID 14923Ammonium HydroxideHCID 517165Ammonium Acetate2×

Product 1

HCID 59557418Ethyl 3-amino-4-methyl-pent-2-enoate

Procedure

To 100 g (0.63 mol) of ethyl isobutyryl acetate was added ammonium acetate (68.2 g, 0.89 mol), cyclohexane (230 mL) and isopropanol (74 mL). The mixture was heated at reflux under argon atmosphere with a Dean-Stark trap. After 2 hours, a second portion of ammonium acetate (14.6 g, 0.19 mol) was added to the reaction. The reaction was heated at reflux for 12 hours and then allowed to cool to room temperature. A total of ˜30 mL of water was collected in the Dean-Stark trap. An ice bath was used to cool the reaction to 10° C. and then ammonium hydroxide (63 mL) was added dropwise. The organic layer was separated, dried with sodium sulfate, filtered, and concentrated to yield a yellow oil. The crude product (90.9 g, 0.58 mol, 92%) was taken directly to the next step without any further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon atmosphere with a Dean-Stark trap
  3. temperatureThe reaction was heated
  4. temperatureat reflux for 12 hours
  5. customA total of ˜30 mL of water was collected in the Dean-Stark trap
  6. customAn ice bath was used
  7. temperatureto cool
  8. customthe reaction to 10° C.
  9. customThe organic layer was separated
  10. dry with materialdried with sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto yield a yellow oil

Sources & evidence

ORD record
ord-6d860f2537824a04963bbe31dafe5a49
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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