2-(5,6-Dichloro-pyridine-2-carbonyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester → HCID 58017253, compound

HRID 1895027Notes

Reaction equation

HRID 1895027 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[N:19]=1)=[O:17])[CH2:13][CH2:14][CH3:15])=O)(C)(C)C>Cl.CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([C:9]2([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:17])=[N:19][C:20]=1[Cl:25]

Participants

4

Reactant 1

HCID 866208622-(5,6-Dichloro-pyridine-2-carbonyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58017253HCID 58017253, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-(5,6-dichloro-pyridine-2-carbonyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.280 g, 0.725 mmol) in 1N HCl in MeOH (3 mL) was stirred at ambient temperature under nitrogen for 20 hours. The reaction mixture was concentrated in vacuo and the resulting residue was purified by chromatography (silica, 0 to 30% MeOH in DCM) to yield (5,6-dichloro-pyridin-2-yl)-(2-propyl-pyrrolidin-2-yl)-methanone (0.167 g, 0.522 mmol, 72%) as a yellow solid and as a monohydrochloride salt, MS=287 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was purified by chromatography (silica, 0 to 30% MeOH in DCM)

Sources & evidence

ORD record
ord-624bea1c108d415bb8c2d2d717dfd7e8
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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