HCID 86607612, compound → HCID 68452652, compound

HRID 2357607Notes

Reaction equation

HRID 2357607 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 (3.0g, 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, then concentrated in vacuo and NaOH—about 5N (30 mL) was added. The mixture was stirred for 2 h at 60° C., then cooled, washed with EtOAc (30 mL) and acidified to ˜pH 5 with conc HCl. The mixture was extracted into dichloromethane, which was separated, dried over sodium sulfate, and concentrated via rotovap to give the title compound. Found MS (ES+): 214 (M+H)+.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated to 90° C. for 3 h
  3. concentrationconcentrated in vacuo and NaOH—about 5N (30 mL)
  4. additionwas added
  5. temperaturecooled
  6. washwashed with EtOAc (30 mL)
  7. extractionThe mixture was extracted into dichloromethane, which
  8. customwas separated
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-56d0b25693d34d98bba134f067d7d7f0
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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