Gamma-Butyrolactone → HCID 40530849, compound

HRID 323434Notes

Reaction equation

HRID 323434 reaction equation
[C:1]1(=[O:6])O[CH2:4][CH2:3][CH2:2]1.[CH3:7][C@@H:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(OCC)(=O)C>[CH3:7][C@@H:8]([N:15]1[CH2:4][CH2:3][CH2:2][C:1]1=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 40530849HCID 40530849, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

According the the procedure of J. Am. Chem. Soc., 74, 1952 (1959), combine butyrolactone (8.6 g, 100 mmol) and (R)-α-methylbenzylamine (15.0 g, 123 mmol) and heat to 180° C. After 48 hours, heat to 210° C. After 6 hours, cool the reaction mixture and evaporate in vacuo using a short path distillation apparatus to obtain a residue: bp 110° C. at 0.5 mm Hg. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.45 (silica gel, ethyl acetate).

Workup

  1. temperatureheat to 210° C
  2. waitAfter 6 hours
  3. temperaturecool the reaction mixture
  4. customevaporate in vacuo
  5. distillationa short path distillation apparatus
  6. customto obtain a residue

Sources & evidence

ORD record
ord-2c4dc08e83f448c8b1e76530cd1e9188
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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