HCID 67442636, compound → HCID 67441232, compound

HRID 1715081Notes

Reaction equation

HRID 1715081 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 67442636HCID 67442636, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67441232HCID 67441232, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3R,3aR,6R,6aS)-(9H-Fluoren-9-yl)methyl 3-hydroxy-6-methoxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (5b). Ethanol (30 mL) was added dropwise to a mixture of 10% palladium on charcoal (200 mg) and syn-/anti-epoxides respectively (605 mg, 2.06 mmol) under an atmosphere of argon. The argon was replaced by hydrogen then the suspension was stirred for 2.5 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,6R,6aS)-6-methoxyhexahydro-2H-furo[3,2-b]pyrrol-3-ol which was used without further purification.

Workup

  1. filtrationthen filtered through celite in vacuo
  2. washThe filter cake was washed with ethanol
  3. customthe solvents removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-ff3fc04425a6409b9cf5b28449350a40
Source dataset
uspto-grants-2010_09
Patent number
US07799791B2

Reaction notes

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