HCID 86759177, compound → 2-Pyrrolidinone,4-cyclopentyl-(9CI)

HRID 1169191Notes

Reaction equation

HRID 1169191 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([CH2:12][N:13]=[N+]=[N-])[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C>CO.[Ni]>[CH:7]1([CH:6]2[CH2:12][NH:13][C:4](=[O:3])[CH2:5]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 86759177HCID 86759177, compound

Product 1

HCID 121151672-Pyrrolidinone,4-cyclopentyl-(9CI)Yield 58.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Preparation of 4-Cyclopentyl-pyrrolidin-2-one—A solution of 3-azidomethyl-3-cyclopentyl-propionic acid ethyl ester (3.7 g, 16.7 mmol) in 50 mL of MeOH is treated with Raney Nickel under an H2 atmosphere at room temperature. When the theoretical amount of H2 is taken up, the catalyst is removed by filtration and MeOH is evaporated. The remaining solid is recrystallized from hexanes to give 1.5 g (58% yield) of 4-cyclopentyl-pyrrolidin-2-one; mp=117-119° C. NMR (1H, 400 MHz, CDCl3) δ1.1 (2H, m); 1.4-1.6 (4H, m); 1.7 (3H, m); 2.1 (1H, m); 2.3 (1H, m); 2.4 (1H, m); 3.05 (1H, dd); 3.4 (1H, dd). Analysis for C9H15NO: Calculated: C,70.55; H,9.87; N,9.14. Found: C, 70.80; H,9.47; N,9.09.

Workup

  1. customthe catalyst is removed by filtration and MeOH
  2. customis evaporated
  3. customThe remaining solid is recrystallized from hexanes

Sources & evidence

ORD record
ord-f31cf20ffb114ad4b0c41d0bde2fc8c4
Source dataset
uspto-grants-2003_09
Patent number
US06627771B1

Reaction notes

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