Dicyclohexylcarbodiimide → 3-(3-Pyridyl)-1-propyl N-(tert-butyloxycarbonyl)pyrrolidine-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Dicyclohexylcarbodiimide	HCID 10868	—
Reactant	3-Pyridinepropanol	HCID 17861	—
Reactant	Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-	HCID 18462	—
Reactant	1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-	HCID 85083	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(3-Pyridyl)-1-propyl N-(tert-butyloxycarbonyl)pyrrolidine-2-carboxylate	HCID 53885642	53.4%

Reaction Steps

A mixture of N-(tert-butyloxycarbonyl)-(S)-proline (6.0 g; 28 mmol); 3-(3-pyridyl)-1-propanol (5.80 g; 41.8 mmol), dicyclohexylcarbodiimide (9.20 g; 44.48 mmol), camphorsulfonic acid (21.60 g; 9.26 mmol) and 4-dimethylaminopyridine (1.12 g; 9.26 mmol) in dry methylene chloride (200 mL) was stirred overnight. The reaction mixture was filtered through Celite, concentrated, and purified on a silica gel column eluting with 40% ethyl acetate in hexane to obtain 5.0 g of the product as a clear oil (53%), 1H NMR (300 MHz, CDCl3): δ 1.42 (s, 9H); 1.43-1.95 (m, 6H); 2.68 (m, 2H); 3.46-3.52 (m, 2H); 4.11-4.22 (m, 2H); 4.33 (m, 1H); 7.17-7.24 (m, 1H); 7.47 (m, 1H); 8.43 (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05968957
Source dataset	uspto-grants-1999_10
ORD ID	ord-be712b6af76d4ab6b410e4105a8f5dd5
Source note	uspto-grants-1999_10