Dichloromethane → (3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one

HRID 1396640Notes

Reaction equation

HRID 1396640 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@H:8]1[C@H:12]2[O:13][CH2:14][C@@H:15]([OH:16])[C@H:11]2[O:10][CH2:9]1.C(Cl)Cl>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@@H:8]1[CH2:9][O:10][C@@H:11]2[C:15](=[O:16])[CH2:14][O:13][C@H:12]12

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86718453(3R,3aR,6R,6aR)-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 86718460(3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one

Reagents, catalysts & solvents 1

HCID 178419074HCID 178419074, compoundCatalyst

Procedure

To 1.4 g (5.0 mmol) (3R,3aR,6R,6aR)-6-(5-fluoro-2-nitro-phenoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (III.1), 2.5 g molecular sieves 4 Å in DCM 1.2 g (10.0 mmol) N-methyl-morpholin-N-oxide and after 5 min 0.1 g (0.25 mmol) tetrapropylammonium perruthenate are added. The reaction mixture is stirred at RT for 30 min and purified by FC.

Workup

  1. custompurified by FC

Sources & evidence

ORD record
ord-d96f984788924b2d858246eafc09b762
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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