Tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate → HCID 68953107, compound

HRID 2384930Notes

Reaction equation

HRID 2384930 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[O:21])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 67239763Tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate

Product 1

HCID 68953107HCID 68953107, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Stir a solution of 3-(4-bromo-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.79 g, 10.7 mmol) in 4 M HCl in dioxane (21.4 mL) at 0° C. for one hour. 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 chromatograph, eluting with 5-10% in MeOH (2N NH3)/CH2Cl2 to give 2.24 g (82%) of the title compound. LC-MS m/z (79Br) 254.0 [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 chromatograph
  10. washeluting with 5-10% in MeOH (2N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-296658d0ff634a36a141ca9faa3afee6
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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