Borane → HCID 57758664, compound

HRID 229525Notes

Reaction equation

HRID 229525 reaction equation
[OH:1][CH:2]1[C:6](=O)[N:5]([C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH2:4][C@:3]1([CH3:23])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].B>O1CCCC1>[OH:1][CH:2]1[CH2:6][N:5]([C@@H:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[CH2:4][C@:3]1([CH3:23])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 6331BoraneHCID 57758671HCID 57758671, compound

Product 1

HCID 57758664HCID 57758664, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl(3S)-4-hydroxy-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (5.13 g, 16.1 mmol) in tetrahydrofuran (100 mL), 1.17M solution of borane in tetrahydrofuran (45.3 mL, 53.1 mmol) was added in an ice bath, and the mixture was stirred at room temperature for 13 hours. After concentrating the reaction mixture under reduced pressure, water (10 mL), ethanol (100 mL), and triethylamine (5 mL) were added to the concentrate, and the mixture was heated under reflux in an oil bath at 90° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and water (200 mL) was added to the concentrate. The mixture was extracted with ethyl acetate (200 mL ×2). The resulting organic layer was washed with saturated aqueous solution of sodium chloride (200 mL), and dried with anhydrous sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1→1:2) to obtain 1.50 g (31%) of the title compound as a colorless oily substance.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure, water (10 mL), ethanol (100 mL), and triethylamine (5 mL)
  2. additionwere added to the concentrate
  3. temperaturethe mixture was heated
  4. temperatureunder reflux in an oil bath at 90° C. for 2 hours
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and water (200 mL)
  6. additionwas added to the concentrate
  7. extractionThe mixture was extracted with ethyl acetate (200 mL ×2)
  8. washThe resulting organic layer was washed with saturated aqueous solution of sodium chloride (200 mL)
  9. dry with materialdried with anhydrous sodium sulfate
  10. filtrationAfter the filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1→1:2)

Sources & evidence

ORD record
ord-e32f799ff49c49dca0c57cff8002d226
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

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