Hydrochloric Acid → HCID 68430203, compound

HRID 1162830Notes

Reaction equation

HRID 1162830 reaction equation
Cl.[C:2]1([CH:8]2[N:12]3[C:13](=[O:17])[CH2:14][NH:15][CH2:16][CH:11]3[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:27]([N:30]=[C:31]=[O:32])([CH3:29])[CH3:28]>ClCCl>[CH:27]([NH:30][C:31]([N:15]1[CH2:14][C:13](=[O:17])[N:12]2[C@@H:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10][C@H:11]2[CH2:16]1)=[O:32])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 77498114HCID 77498114, compound

Product 1

HCID 68430203HCID 68430203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the HCl salt of racemic-(6R,8aS)-6-phenylhexahydropyrrolo[1,2-a]pyrazin-4(1H)-one (0.25 g, 0.99 mmol) and DIEA (0.345 mL, 1.99 mmol) in dichloromethane (4 mL) at ambient temperature was added isopropyl isocyanate (0.146 mL, 1.48 mmol). The mixture was stirred at ambient temperature for 18 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and brine. The EtOAc layer was separated, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Concentration of appropriate fractions afforded (6R,8aS)-N-isopropyl-4-oxo-6-phenylhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide. HPLC RT=2.68 min (Method A); ES MS (M+H)=302.3.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and brine
  3. customThe EtOAc layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was subjected to HPLC purification on C-18 stationary phase
  8. washeluted with water/acetonitrile/TFA mobile phase

Sources & evidence

ORD record
ord-b472b969ae534fa5974947eec182f94f
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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