HCID 46193050, compound → HCID 57551911, compound

HRID 333029Notes

Reaction equation

HRID 333029 reaction equation
[Cl:1][C@H:2]1[CH2:6][N:5](C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[C@@H:4]2[C@@H:24]([OH:27])[CH2:25][O:26][C@H:3]12.Cl[C@H]1CN(C(OCC2C=CC=CC=2)=O)[C@@H]2[C@@H](O)CO[C@H]12.[H][H]>[Pd].C(O)C>[Cl:1][C@H:2]1[CH2:6][NH:5][C@@H:4]2[C@@H:24]([OH:27])[CH2:25][O:26][C@H:3]12

Participants

6

Reactant 3

HCID 46193050HCID 46193050, compoundHCID 57792824HCID 57792824, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57551911HCID 57551911, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3R, 3aR, 6S, 6aS)-(9H-Fluoren-9-yl)methyl 6-chloro-3-hydroxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (70). Ethanol (8.5 mL) was added dropwise to a mixture of 10% palladium on charcoal (55 mg) and alcohol (68) (550 mg, 1.85 mmol) under an atmosphere of argon. The argon was replaced by hydrogen then the suspension was stirred for 1 hour 35 minutes before filtering the mixture through celite in vacuo. The filter cake was washed with ethanol (45 mL) then the solvents removed in vacuo from the filtrate. The residue was azeotroped with toluene (3×5 mL) to obtain (3R, 3aR, 6S, 6aS)-6-chlorohexahydro-2H-furo[3,2-b]pyrrol-3-ol (69) which was used without further purification.

Workup

  1. filtrationbefore filtering the mixture through celite in vacuo
  2. washThe filter cake was washed with ethanol (45 mL)
  3. customthe solvents removed in vacuo from the filtrate
  4. customThe residue was azeotroped with toluene (3×5 mL)

Sources & evidence

ORD record
ord-73f8a312c7024328953478ed1ee53b60
Source dataset
uspto-grants-2014_11
Patent number
US08877927B2

Reaction notes

Loading…