Nicotinic Acid → 1-(Pyridine-3-carbonyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 82488

Reaction equation

[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([C:7]([OH:9])=O)[CH:2]=1.[CH3:10][O:11][C:12](=[O:18])[C@@H:13]1[CH2:17][CH2:16][CH2:15][NH:14]1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:10][O:11][C:12]([CH:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:7]([C:3]1[CH:4]=[N:5][CH:6]=[CH:1][CH:2]=1)=[O:9])=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of niacin (0.4 g 3.50 mmol) in DCM (10 mL) were added L-proline methyl ester (0.5 g, 3.21 mmol), N-methyl morpholine (1.1 mL, 0.10.5 mmol), EDC.HCl (1.2 g, 6.4 mmol) and catalytic amount of DMAP at ice temperature (0° C.). The mixture was allowed to stir at room temperature (25° C.) over a period of 2 h. The resulting mixture diluted with DCM (100 mL) washed with water (2×100 mL) and dried over sodium sulphate. Solvent was evaporated under reduced pressure to obtain product as yellow gummy oil (1.3 g).

Workup

washwashed with water (2×100 mL)
dry with materialdried over sodium sulphate
customSolvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3733038fe77a4ef3b693f11951fb0d39
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846721B2

Linked notes

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