HCID 86607612, compound → HCID 68452652, compound

HRID 2357623Notes

Reaction equation

HRID 2357623 reaction equation
O[C:2]1([CH3:18])[N:6]([C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[C@@H:5]([C:13]([O:15]CC)=[O:14])[CH2:4][CH2:3]1>FC(F)(F)C(O)=O>[CH2:10]([O:9][C:7]([N:6]1[CH:2]([CH3:18])[CH2:3][CH2:4][C@@H:5]1[C:13]([OH:15])=[O:14])=[O:8])[CH:11]=[CH2:12]

Participants

3

Reactant 1

HCID 86607612HCID 86607612, compound

Product 1

HCID 68452652HCID 68452652, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

(R)-1-allyl 2-ethyl 5-hydroxy-5-methylpyrrolidine-1,2-dicarboxylate (3.0 g, 12 mmol) was dissolved in trifluoroacetic acid (20 mL) and cooled to 0° C. before borane-pyridine complex (2.9 mL, 23 mmol) was added. The reaction mixture was heated to 90° C. for 3 h before it was concentrated in vacuo and NaOH −5 N (30 mL) was added. The mixture was stirred for 2 h at 60° C., then cooled, washed with ethyl acetate (30 mL), acidified to ˜pH 5 with conc HCl, extracted with dichloromethane, separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 214 (M+H)+.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated to 90° C. for 3 h before it
  3. concentrationwas concentrated in vacuo and NaOH −5 N (30 mL)
  4. additionwas added
  5. temperaturecooled
  6. washwashed with ethyl acetate (30 mL)
  7. extractionextracted with dichloromethane
  8. customseparated
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea1fce2a75034ed1984c23a22a27dcbe
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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