HCID 57899288, compound → HCID 57899289, compound

HRID 1802794Notes

Reaction equation

HRID 1802794 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57899288HCID 57899288, compound

Product 1

HCID 57899289HCID 57899289, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-2-[4-((E)-2-Methoxycarbonyl-vinyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (2.4 g, 7.242 mmol) was dissolved in ethanol (100 mL), and wet 10% Pd/C added. The reaction mixture was placed under an atmosphere of hydrogen for 4 hrs (Parr apparatus, 25 psi) then filtered through a plug of celite and concentrated to dryness to give (R)-2-[4-(2-methoxycarbonyl-ethyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil (2.4 g, 7.2 mmol, >99% yield).

Workup

  1. filtration(Parr apparatus, 25 psi) then filtered through a plug of celite and
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5e16abc5c4ba40419eedb3af6f45de86
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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