Oxygen → HCID 67490777, compound

HRID 1917387Notes

Reaction equation

HRID 1917387 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:31][CH:32]=C)[C@H:12]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:22])[N:10]([C@@H:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:34]=O.[BH4-].[Na+].[Cl-].[NH4+]>CO>[C:1]([O:5][C:6]([C@@:8]1([CH2:31][CH2:32][OH:34])[C@H:12]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:22])[N:10]([C@@H:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:24])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 977OxygenHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67490890HCID 67490890, compound

Product 1

HCID 67490777HCID 67490777, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (3S,4R)-3-allyl-4-benzyloxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (8.00 g, 17.8 mmol) in methanol (177 mL) was bubbled with oxygen for 10 minutes. After bubbling with ozone for 30 minutes with stirring under cooling with dry ice-methanol, ozone was removed by bubbling with nitrogen. Sodium borohydride (1.68 g, 44.4 mmol) was added under cooling with ice-acetone, and the mixture was stirred under cooling for 1.5 hours. A saturated ammonium chloride solution (150 mL) was added to the reaction solution, and methanol was evaporated by concentration under reduced pressure. The mixture was extracted with ethyl acetate (200 mL×1, 150 mL×1). The organic layer was washed with brine (300 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→66:34→50:50) to give 3.79 g of the title compound as a pale yellow oil.

Workup

  1. customAfter bubbling with ozone for 30 minutes
  2. temperatureunder cooling with dry ice-methanol, ozone
  3. customwas removed
  4. customby bubbling with nitrogen
  5. stirringthe mixture was stirred
  6. temperatureunder cooling for 1.5 hours
  7. customwas evaporated by concentration under reduced pressure
  8. extractionThe mixture was extracted with ethyl acetate (200 mL×1, 150 mL×1)
  9. washThe organic layer was washed with brine (300 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationAfter filtration
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→66:34→50:50)

Sources & evidence

ORD record
ord-7d70ebf97a5a4b61a0ff0b6c12e01184
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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