Uses
(+/-)-3-(Boc-amino)pyrrolidine is the homochiral starting materials utilised in the synthesis of all of the chiral compounds. Reactant in the peptide activated G-protein coupled receptors test.
Synthesis
General procedure for the synthesis of 3-(Boc-amino)pyrrolidine from 1-benzyl-3-(Boc-amino)pyrrolidine: 1-benzyl-3-(Boc-amino)pyrrolidine (15.75 g, 57.0 mmol) was dissolved in a solvent mixture of methanol and tetrahydrofuran (4:1, 114 ml) in a 500 ml reaction vessel. A catalytic amount of 10% palladium/carbon (Pd/C) was added to the solution. The reaction mixture was stirred and reacted for 12 hours under hydrogen atmosphere. Upon completion of the reaction, the palladium/carbon catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography to afford 3-(Boc-amino)pyrrolidine (9.51 g, 99% yield). The product was characterized by 1H-NMR (200 MHz, CDCl3): δ 1.41 (s, 9H), 2.26 (m, 2H), 2.55 (m, 3H), 2.74 (m, 1H), 4.84 (br, 1H).LC-MS analysis showed [M+H]+ peak of 187.
References
[1] Patent: WO2008/54154, 2008, A1. Location in patent: Page/Page column 76; 81; 162-163; 168
[2] Patent: WO2007/52938, 2007, A1. Location in patent: Page/Page column 23
[3] Patent: US5281612, 1994, A
[4] Patent: US4604401, 1986, A
[5] Patent: US4617308, 1986, A
