Tetrahydrofuran → Compound 10

HRID 651109Notes

Reaction equation

HRID 651109 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12]C=CC1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:17]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].[O:28]1[CH2:32][CH2:31][CH2:30]C1>[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:30][C@H:31]([OH:17])[C@H:32]([OH:28])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 13329883Compound 10

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

A solution of crude 2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (10.5 g, 62.1 mmol) in tetrahydro-furan (300 ml) was treated sequentially with osmium tetroxide (2.5% in t-butanol, 6 mL) and N-methylmorpholine-N-oxide at 25° C. After 48 hours, aqueous 10% sodium thiosulfate solution was added and the mixture was stirred 30 minutes, partially concentrated to remove tetrahydro-furan, and the resulting aqueous mixture extracted twice with ether. The ether extracts were washed with 10% sodium thiosulfate, 0.1 N HCl, dried and concentrated giving a dark orange oil which was chromatographed on silica eluted with 1%, 2%, 4%, 8% and 10% ethanol-dichloromethane giving an amber syrup (4.09 g).

Workup

  1. concentrationpartially concentrated
  2. customto remove tetrahydro-furan
  3. extractionthe resulting aqueous mixture extracted twice with ether
  4. washThe ether extracts were washed with 10% sodium thiosulfate, 0.1 N HCl
  5. customdried
  6. concentrationconcentrated
  7. customgiving a dark orange oil which
  8. customwas chromatographed on silica
  9. washeluted with 1%, 2%, 4%, 8% and 10% ethanol-dichloromethane giving an amber syrup (4.09 g)

Sources & evidence

ORD record
ord-3c859eaa618648deb7572519482a49c9
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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