Cyclopropylamine → HCID 66705180, compound

HRID 2108794Notes

Reaction equation

HRID 2108794 reaction equation
[C:1]1([C@H:7]([N:9]2[CH2:16][C@@H:15]3[C@@H:11]([CH2:12][O:13][C:14]3=[O:17])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C(O)C>[CH:18]1([NH:21][C:14]([C@@H:15]2[C@H:11]([CH2:12][OH:13])[CH2:10][N:9]([C@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH3:8])[CH2:16]2)=[O:17])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 66705207HCID 66705207, compound

Product 1

HCID 66705180HCID 66705180, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

(1S,5R)-7-[(1R)-1-Phenylethyl]-3-oxa-7-azabicyclo[3.3.0]octane-2-one (7.73 g, 33.4 mmol) was dissolved in ethanol (92 mL). To this solution, cyclopropylamine (46.3 ml) was added and the mixture was stirred at 80° C. for 44 hours and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed with water (2×50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Diisopropylether (300 mL) was added to the residue and the solution was heated to form crystals. The solution was concentrated to approximately half the original volume and the crystals formed were filtered. The collected crystals were washed with diisopropyl ether and were dried under reduced pressure to give (3R,4S)-N-cyclopropyl-4-hydroxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide as white crystals (4.41 g). The filtrate and the washings were then combined and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=1:1->ethyl acetate) to give additional (3R,4S)-N-cyclopropyl-4-hydroxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide (1.50 g).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  3. washwashed with water (2×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionDiisopropylether (300 mL) was added to the residue
  7. temperaturethe solution was heated
  8. customto form crystals
  9. concentrationThe solution was concentrated to approximately half the original volume
  10. customthe crystals formed
  11. filtrationwere filtered
  12. washThe collected crystals were washed with diisopropyl ether
  13. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-2d03c4cc840a4f24b7af018b5602c643
Source dataset
uspto-grants-2009_04
Patent number
US07514451B2

Reaction notes

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