Hydrochloric Acid → HCID 58092703, compound

HRID 1430114Notes

Reaction equation

HRID 1430114 reaction equation
Cl.[CH3:2][C@@:3]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4]1>C(O)CCC>[CH2:2]([O:9][C:8]([C@:3]1([CH3:2])[CH2:7][CH2:6][CH2:5][NH:4]1)=[O:10])[CH2:3][CH2:7][CH3:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69936642-Methyl-L-proline

Product 1

HCID 58092703HCID 58092703, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Concentrated HCl (2 ml) is added to a suspension of (S)-2-methyl-pyrrolidine-2-carboxylic acid (2 g) in butan-1-ol (50 ml) which is heated at 60° C. for 18 hours then at reflux for 4 days. The reaction mixture is evaporated, partitioned between saturated aqueous NaHCO3 and CH2Cl2, extracted 3×CH2Cl2, dried over Na2SO4 and evaporated. The isolated oil is then kugelrohr distilled at 10 mbar to give the title compound as a clear colorless oil from the fraction distilling at an oven temperature of 100-120° C.

Workup

  1. temperatureat reflux for 4 days
  2. customThe reaction mixture is evaporated
  3. custompartitioned between saturated aqueous NaHCO3 and CH2Cl2
  4. extractionextracted 3×CH2Cl2
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. distillationThe isolated oil is then kugelrohr distilled at 10 mbar

Sources & evidence

ORD record
ord-c63ac4d64577403bbf22e709bd98a52a
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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