HCID 57551959, compound → HCID 59807331, compound

HRID 333031Notes

Reaction equation

HRID 333031 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 57551959HCID 57551959, compoundHCID 57792812HCID 57792812, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59807331HCID 59807331, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation of (3R, 3aR, 6R, 6aS)-(9H-Fluoren-9-yl)methyl 6-chloro-3-hydroxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (78). Ethanol (3.5 mL) was added dropwise to a mixture of 10% palladium on charcoal (25 mg) and (3R, 3aR, 6R, 6aS)-benzyl 6-chloro-3-hydroxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (198 mg, 0.67 mmol) under an atmosphere of argon. The argon was replaced by hydrogen then the suspension was stirred for 4.5 hours before filtering the mixture through celite in vacuo. The filter cake was washed with ethanol (20 mL) then the solvents removed in vacuo from the filtrate. The residue was azeotroped with toluene (3×5 mL) to obtain (3R, 3aR, 6R, 6aS)-6-chlorohexahydro-2H-furo[3,2-b]pyrrol-3-ol (77) which was used without further purification.

Workup

  1. filtrationbefore filtering the mixture through celite in vacuo
  2. washThe filter cake was washed with ethanol (20 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-b04e12f686f044dcb2d7ec7267087bf2
Source dataset
uspto-grants-2014_11
Patent number
US08877927B2

Reaction notes

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