Tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenylethynyl]-pyrrolidine-1-carboxylate → Tert-butyl 2-{2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenyl]-ethyl}-pyrrolidine-1-carboxylate

HRID 715971Notes

Reaction equation

HRID 715971 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]([NH:5][C:6]1[C:7]([C:26]([O:28][CH3:29])=[O:27])=[C:8]([C:12]#[C:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:9]=[CH:10][CH:11]=1)=[O:4]>C(O)C.[Pd]>[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]([NH:5][C:6]1[C:7]([C:26]([O:28][CH3:29])=[O:27])=[C:8]([CH2:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 1

HCID 70982938Tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenylethynyl]-pyrrolidine-1-carboxylate2×

Product 1

HCID 70984356Tert-butyl 2-{2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenyl]-ethyl}-pyrrolidine-1-carboxylateYield 85.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenylethynyl]-pyrrolidine-1-carboxylate (Intermediate 38, 3.71 g) in ethanol (100 mL) was treated with 10% palladium on carbon (0.50 g) and stirred under an atmosphere of hydrogen for 4 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give tert-butyl 2-{2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenyl]-ethyl}-pyrrolidine-1-carboxylate (3.21 g) as a colourless gum.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica
  4. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

Sources & evidence

ORD record
ord-d379d8d8e56845399a991e033138c23c
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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