3-(5-Bromo-pyridine-2-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → (5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl-methanone

HRID 423394Notes

Reaction equation

HRID 423394 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=2)=[O:14])[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[O:14])=[N:16][CH:17]=1

Participants

4

Reactant 1

HCID 666738453-(5-Bromo-pyridine-2-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66673744(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl-methanoneYield 87.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Stir a solution of 3-(5-bromo-pyridine-2-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.65 g, 1.8 mmol) in 4 M HCl in dioxane (3.7 mL) at 0° C. for 1 h. Concentrate the reaction mixture, dilute the mixture with CH2Cl2, wash with 5 N NaOH (15 mL), and back-extract the aqueous with CH2Cl2. Wash the combined organic layer with brine, dry over Na2SO4, filter and concentrate. Purify the crude material by flash chromatography, eluting with 10% MeOH (2N NH3)/CH2Cl2 to give 0.4 g (85%) of the title compound. LC-MS/ES m/z (81Br) 257.0 [M+H]+.

Workup

  1. concentrationConcentrate the reaction mixture
  2. additiondilute the mixture with CH2Cl2
  3. washwash with 5 N NaOH (15 mL)
  4. extractionback-extract the aqueous with CH2Cl2
  5. washWash the combined organic layer with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude material by flash chromatography
  10. washeluting with 10% MeOH (2N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-97d0e22fa15a4b3eb00b208cbd0103ec
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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