HCID 69890832, compound → HCID 10965467, compound

HRID 353373Notes

Reaction equation

HRID 353373 reaction equation
C(OC([NH:11][C@:12]1([C:22]([OH:24])=[O:23])[C@@H:17]2[CH2:18][C@@:14]3([C:19]([OH:21])=[O:20])[C@@H:15]([CH2:16]2)[C@@H:13]13)=O)C1C=CC=CC=1.[H][H]>C(O)C.O.[Pd]>[NH2:11][C@:12]1([C:22]([OH:24])=[O:23])[C@@H:17]2[CH2:18][C@@:14]3([C:19]([OH:21])=[O:20])[C@@H:15]([CH2:16]2)[C@@H:13]13

Participants

5

Reactant 2

HCID 69890832HCID 69890832, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10965467HCID 10965467, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 1.1 g (3.3 mmole) of (+/−)-(1R*,2R*,3R*,4S*,6S*)-3-benzyloxycarbonylamino-tricyclo[2.2.1.02,6]heptane-1,3-dicarboxylic acid in 100 mL of 1:1 ethanol/water was added 0.25 g of 10% palladium on carbon. The mixture was treated with 60 psi of hydrogen on a Parr apparatus for 24 hours. The catalyst was removed by filtration through celite and the filtrate was concentrated in vacuum to give 0.18 g of the title compound as a gray solid sesquihydrate. Extraction of the catalyst and celite with boiling water, filtration of the extracts through a millipore filter and concentration in vacuum led to the isolation of an additional 0.32 g of white solid. This was recrystallized from water to give 0.21 g of the title compound as a white crystalline one-quarter hydrate, m.p.>250° C.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-b46ea2d155db4b2bab503b568aa4765b
Source dataset
uspto-grants-2004_06
Patent number
US06750364B2

Reaction notes

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