HCID 68433232, compound → HCID 59568712, compound

HRID 1187046Notes

Reaction equation

HRID 1187046 reaction equation
C1(COC([N:11]2[CH2:16][CH:15]3[CH2:17][CH:12]2[CH2:13][N:14]3[CH2:18][CH:19]([OH:31])[C:20]2[CH:29]=[CH:28][C:23]3[C:24](=[O:27])[O:25][CH2:26][C:22]=3[C:21]=2[CH3:30])=O)C=CC=CC=1>CCOC(C)=O.[Pd]>[CH:15]12[CH2:17][CH:12]([NH:11][CH2:16]1)[CH2:13][N:14]2[CH2:18][CH:19]([C:20]1[CH:29]=[CH:28][C:23]2[C:24](=[O:27])[O:25][CH2:26][C:22]=2[C:21]=1[CH3:30])[OH:31]

Participants

4

Reactant 1

HCID 68433232HCID 68433232, compound

Product 1

HCID 59568712HCID 59568712, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of isomers B of phenylmethyl-5-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (470 mg, 1.114 mmol) in 50 mL of EtOAc was added 100 mg of Pd/C under Ar, and the mixture was stirred at ambient temperature under H2 atmosphere overnight. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by prep-TLC (MeOH/DCM=1:15) to give isomers B of 5-[2-(2,5-diazabicyclo[2.2.1]hept-2-yl)-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one. MS m/z 289 (M+1)−.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by prep-TLC (MeOH/DCM=1:15)

Sources & evidence

ORD record
ord-e4c5e625169e4c5eb7235d34e1e024cb
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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