Triethylamine → (S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Isobutyl chloroformate	HCID 62365	—
Reactant	1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-	HCID 85083	—
Reactant	HCID 178509779	HCID 178509779	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester	HCID 69619344	44%

Reaction Conditions

Temperature	120 °C

Reaction Steps

(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (698 mg, 44%) was prepared according to the procedure in Example 25 from (S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1.00 g, 4.66 mmol) with isobutyl chloroformate (0.64 mL, 4.9 mmol) and triethylamine (1.6 mL, 11.5 mmol) in THF (14 mL). Then 3-cyano-N-hydroxy-benzamidine (753 mg, 4.67 mmol) and DMF (15 mL) were added and the mixture was heated at 120° C. for 18 h.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07074809B2
Source dataset	uspto-grants-2006_07
ORD ID	ord-03587de826fc494386ac1305b85cf946
Source note	uspto-grants-2006_07