Hydrochloric Acid → HCID 58092703, compound

HRID 1807653Notes

Reaction equation

HRID 1807653 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) was added to a suspension of (S)-2-methyl-pyrrolidine-2-carboxylic acid (2 g) in butan-1-ol (50 ml) which was heated at 60° C. for 18 h then at reflux for 4 days. The RM was evaporated, partitioned between saturated aqueous NaHCO3 and DCM, extracted 3× with DCM, dried over Na2SO4 and evaporated. The isolated oil was 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 RM was evaporated
  3. custompartitioned between saturated aqueous NaHCO3 and DCM
  4. extractionextracted 3× with DCM
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. distillationkugelrohr distilled at 10 mbar

Sources & evidence

ORD record
ord-6fb64eae2b7f4f27a02d7dfc3fb8cd71
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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