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ChemicalBook CAS DataBase List (S)-1-Cbz-pyrrolidine-3-carboxylic acid
192214-00-9

(S)-1-Cbz-pyrrolidine-3-carboxylic acid synthesis

14synthesis methods
-

Yield: 51%

Reaction Conditions:

with sodium hydroxide in water at 0; for 2 h;

Steps:

46
General procedure: To a solution of 103 20a (500mg, 1.616mmol) in 82 MeOH (13mL) 10% 108 Pd/C (179mg) was added and the mixture was allowed to stir for 20h at 25°C under H2 atmosphere. The reaction was filtered on Celite and the filtrate was concentrated under reduced pressure quantitatively providing (R)-pyrrolidine-3-carboxylic acid submitted to the next step without further purification. To a solution of this latter (460mg, 3.995mmol) in 2N 109 NaOH (2mL) 110 benzylchloroformate (740μL, 5.194mmol) and 4N NaOH (1.5mL) were added and the mixture was stirred at 0°C for 2h. The reaction was extracted with diethyl ether. The aqueous layer was adjusted to pH=2 with 10% HCl at 0°C and extracted with EtOAc. The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography

References:

Ghosh, Arun K.;Brindisi, Margherita;Nyalapatla, Prasanth R.;Takayama, Jun;Ella-Menye, Jean-Rene;Yashchuk, Sofiya;Agniswamy, Johnson;Wang, Yuan-Fang;Aoki, Manabu;Amano, Masayuki;Weber, Irene T.;Mitsuya, Hiroaki [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 19,p. 5114 - 5127]