Tetrahydrofuran → Compound 10

HRID 730062Notes

Reaction equation

HRID 730062 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.[O:21]1[CH2:25][CH2:24][CH2:23]C1>C(O)(C)(C)C.O.O=[Os](=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:23][C@H:24]([OH:17])[C@H:25]([OH:21])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

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

Product 1

HCID 13329883Compound 10

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of N-t-butoxycarbonyl-3-pyrroline (69.3 g) and NMO (72.2 g) in tetrahydrofuran (340 mL), t-butanol (210 mL) and water (100 mL) was added OsO4 (2.5% solution in t-butanol, 4.8 mL), the mixture was heated under reflux for 2.5 hours, and then concentrated in vacuo. After dilution of the residue with brine, the mixture was extracted with ethyl acetate. The organic extracts were concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=1:1) of the residue gave

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationconcentrated in vacuo
  4. extractionAfter dilution of the residue with brine, the mixture was extracted with ethyl acetate
  5. concentrationThe organic extracts were concentrated in vacuo
  6. customFlash chromatography (silica, hexane:ethyl acetate=1:1) of the residue gave

Sources & evidence

ORD record
ord-fdc40ca763044be3acee1952944beda3
Source dataset
uspto-grants-2009_09
Patent number
US07582659B2

Reaction notes

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