HCID 59215873, compound → HCID 59215794, compound

HRID 2245455Notes

Reaction equation

HRID 2245455 reaction equation
C1(COC([NH:11][CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH:18]([C:24]([O:26]CC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=O)C=CC=CC=1>CCO.[Pd]>[O:26]=[C:24]1[CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:14]2[CH2:15][CH2:16][CH2:17][C@H:13]2[CH2:12][NH:11]1

Participants

4

Reactant 1

HCID 59215873HCID 59215873, compound

Product 1

HCID 59215794HCID 59215794, compoundYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

The solution of diethyl {(2S)-2-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinyl}propanedioate (D115, 1.40 g, 3.67 mmol) in EtOH (ca. 20 ml) was degassed, (10%) Pd/C (778 mg, 0.734 mmol) was added and the reaction mixture was stirred under a H2 atmosphere for 2.5 hrs. The catalyst was filtered off and the volume of the filtrated solution was reduced in vacuo. The solution was warmed-up to 50° C. and it was stirred at this temperature for 7 hrs. The solvent was evaporated to dryness to give the title compound as a yellowish oil (793 mg) as a mixture of diastereoisomers. This crude was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. stirringit was stirred at this temperature for 7 hrs
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-315c1e5145334fe7b905ada46b42de82
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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