HCID 86646589, compound → 3-(2-Cyclobutylacetyl)pyrrolidine-1-carboxylic acid tert butyl ester

HRID 1922172Notes

Reaction equation

HRID 1922172 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:19])[CH:14]=[C:15]2[CH2:18][CH2:17][CH2:16]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:19])[CH2:14][CH:15]2[CH2:18][CH2:17][CH2:16]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86646589HCID 86646589, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 866465903-(2-Cyclobutylacetyl)pyrrolidine-1-carboxylic acid tert butyl esterYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add palladium on carbon (50 mg, catalytic) to 3-(2-cyclobutylidene-acetyl)pyrrolidine-1-carboxylic acid tert butyl ester (850 mg, 3.20 mmol) in ethyl acetate (25 mL) and stir under nitrogen at room temperature. Install a balloon of hydrogen gas and stir overnight. Filter the reaction over celite, rinse with ethyl acetate and concentrate to dryness to afford 391 mg (46%) of the desired compound. MS (m/z)=212.0 (M−55)

Workup

  1. filtrationFilter
  2. customthe reaction over celite
  3. washrinse with ethyl acetate
  4. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-92b29a1f4cbe496f8f5460dcbd3656ad
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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