cis-Ethyl 2-(benzylamino)cyclopentanecarboxylate → Ethyl (1R,2S)-2-Aminocyclopentanecarboxylate

HRID 1011509Notes

Reaction equation

HRID 1011509 reaction equation
C([NH:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])C1C=CC=CC=1>[Pd].C(O)C>[NH2:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 1

HCID 10014866cis-Ethyl 2-(benzylamino)cyclopentanecarboxylate

Product 1

HCID 2725068Ethyl (1R,2S)-2-AminocyclopentanecarboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of cis-ethyl 2-(benzylamino)cyclopentanecarboxylate (2.99 g, 12.1 mmol), prepared according to Bartoli, G. et al., J. Org. Chem., 59:5328-5335, was hydrogenated along with 500 mg 10% palladium on carbon in 20 mL ethanol at 45 psi for 22 h. The reaction was filtered through a 45μ filter and concentrated to give cis-ethyl 2-aminocyclopentanecarboxylate (1.75 g, 92%). 1H NMR (400 MHz, CDCl3) δ ppm 4.14 (2H, q, J=7.13 Hz), 3.53-3.62 (1H, m), 2.75 (1H, td, J=8.37, 6.67 Hz), 1.93-2.11 (1H, m), 1.77-1.92 (3H, m), 1.43-1.62 (2H, m), 1.35 (2H, s), 1.25 (3H, t, J=7.18 Hz). MS [M+H]+=158.24.

Workup

  1. filtrationThe reaction was filtered through
  2. filtrationa 45μ filter
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ad6677104f9545ec8087abcf1b74269a
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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