HCID 58256843, compound → HCID 55286288, compound

HRID 2168171Notes

Reaction equation

HRID 2168171 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 58256843HCID 58256843, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 55286288HCID 55286288, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methanol (2.0 mL) was added dropwise to a mixture of 10% palladium on charcoal (20 mg) and bicyclic alcohol (110) (45 mg, 0.162 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,6S,6aR)-6-methylhexahydro-2H-furo[3,2-b]pyrrol-3-ol (109) 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-19bf7224dbe441a08bd1acf9d9d10657
Source dataset
uspto-grants-2015_06
Patent number
US09045492B2

Reaction notes

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