HCID 59145536, compound → HCID 55286287, compound

HRID 1887395Notes

Reaction equation

HRID 1887395 reaction equation
[OH:1][C@@H:2]1[C@H:6]2[N:7](C(OCC3C=CC=CC=3)=O)[CH2:8][C@@H:9]([CH3:10])[C@H:5]2[O:4][CH2:3]1.[H][H]>[Pd].CO>[CH3:10][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 59145536HCID 59145536, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 55286287HCID 55286287, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methanol (1.25 mL) was added dropwise to a mixture of 10% palladium on charcoal (20 mg) and bicyclic alcohol (108) (49 mg, 0.177 mmol) under an atmosphere of argon. The argon was replaced by hydrogen then the suspension was stirred for 1 hour then filtered through celite in vacuo. The filter cake was washed with ethanol (10 mL) then the solvents removed in vacuo from the filtrate. The residue was azeotroped with diethyl ether (3×3 mL) to obtain the crude (3R,3aR,6R,6aR)-6-methylhexahydro-2H-furo[3,2-b]pyrrol-3-ol (107) which was used without further purification.

Workup

  1. filtrationthen filtered through celite in vacuo
  2. washThe filter cake was washed with ethanol (10 mL)
  3. customthe solvents removed in vacuo from the filtrate
  4. customThe residue was azeotroped with diethyl ether (3×3 mL)

Sources & evidence

ORD record
ord-db1b309b3ca2490dbb60499ed2b76cb9
Source dataset
uspto-grants-2013_08
Patent number
US08501744B2

Reaction notes

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