Triethylamine → 1-Aminomethyl-2-isobutyl-cyclopropanecarboxylic acid ethyl ester

HRID 1796821Notes

Reaction equation

HRID 1796821 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:13]#[N:14])[CH2:8][CH:7]1[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:5])[CH3:2].C(N(CC)CC)C>CCO.[Ni]>[CH2:1]([O:3][C:4]([C:6]1([CH2:13][NH2:14])[CH2:8][CH:7]1[CH2:9][CH:10]([CH3:11])[CH3:12])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 695998651-Cyano-2-isobutyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 695998641-Aminomethyl-2-isobutyl-cyclopropanecarboxylic acid ethyl esterYield 26.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-cyano-2-isobutyl-cyclopropanecarboxylic acid ethyl ester (0.41 g, 2.10 mmol) in 45 mL EtOH was added triethylamine (5.0 mL) and Raney nickel (1.0 g). The mixture was hydrogenated in a Parr shaker at 48 psi for 18 hours, filtered, and concentrated. Flash chromatography of the residue (5→10% MeOH/CH2Cl2) provided 0.11 g (26%) of 1-aminomethyl-2-isobutyl-cyclopropanecarboxylic acid ethyl ester as a colorless oil. 1H NMR δ 4.10 (q, J=7.1 Hz, 2H), 2.90 (d, J=14.2 Hz, 1H), 2.76 (d, J=14.2 Hz, 1H), 1.63 (m, 1H), 1.52 (m, 2H), 1.34 (m, 1H), 1.22 (t, J=7.1 Hz, 3H), 1.04 (m, 1H), 0.90 (m, 6H), 0.49 (m, 1H). 13C NMR δ 175.51, 60.75, 42.42, 37.92, 30.61, 29.04, 26.46, 22.91, 22.63, 21.31, 14.49.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d0a50c2ed37a4510a6a54f8912f91ec4
Source dataset
uspto-grants-2006_04
Patent number
US07030267B2

Reaction notes

Loading…