HCID 57792825, compound → HCID 67441691, compound

HRID 1715079Notes

Reaction equation

HRID 1715079 reaction equation
[OH:1][C@@H:2]1[C@H:6]2[N:7](C(OCC3C4C=CC=CC=4C4C3=CC=CC=4)=O)[CH2:8][C@H:9]([O:10][CH3:11])[C@H:5]2[O:4][CH2:3]1.[H][H]>[Pd].C(O)C>[CH3:11][O:10][C@H:9]1[CH2:8][NH:7][C@@H:6]2[C@@H:2]([OH:1])[CH2:3][O:4][C@H:5]12

Participants

5

Reactant 2

HCID 57792825HCID 57792825, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67441691HCID 67441691, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 702EthanolSolvent

Procedure

(3R,3aR,6S,6aS)-(9H-Fluoren-9-yl)methyl 3-hydroxy-6-methoxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (6b). Ethanol (15 mL) was added dropwise to a mixture of 10% palladium on charcoal (30 mg) and anti-(31) (315 mg, 1.07 mmol) under an atmosphere of argon. The argon was replaced by hydrogen then the suspension was stirred for 1.5 hours then 10% palladium on charcoal (30 mg) was added. The mixture was stirred for 2 hours then 10% palladium on charcoal (50 mg) was added. The mixture was stirred for 4.5 hours then filtered through celite in vacuo. The filter cake was washed with ethanol then the solvents removed in vacuo from the filtrate to obtain the crude (3R,3aR,6S,6aS)-6-methoxyhexahydro-2H-furo[3,2-b]pyrrol-3-ol which was used without further purification.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. stirringThe mixture was stirred for 4.5 hours
  3. filtrationthen filtered through celite in vacuo
  4. washThe filter cake was washed with ethanol
  5. customthe solvents removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-7c1011c382884be4adab339d76afbf9c
Source dataset
uspto-grants-2010_09
Patent number
US07799791B2

Reaction notes

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