Trifluoroacetic acid → HCID 53629854, compound

HRID 423399Notes

Reaction equation

HRID 423399 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH2:11][CH2:12][C@@H:8]([NH2:7])[CH2:9]2)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574567861,1-Dimethylethyl N-[(3R)-1-(5-bromo-2-pyridinyl)-3-pyrrolidinyl]carbamate

Product 1

HCID 53629854HCID 53629854, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [(R)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (9.17 g, 26.9 mmol) in CH2Cl2 (45 mL), add TFA (10 mL) and stir at RT overnight. Remove the excess reagent in vacuo. Dilute the residue with CH2Cl2 (100 mL) and wash with 1.0 M NaOH (100 mL). Extract the aqueous layer with CH2Cl2 (3×100 mL). Combine the organic layers, dry with Na2SO4, filter and concentrate to give 6.03 g (93%) of the title compound. MS/ES m/z (79Br) 242 [M+H]+.

Workup

  1. customRemove the excess reagent in vacuo
  2. additionDilute the residue with CH2Cl2 (100 mL)
  3. washwash with 1.0 M NaOH (100 mL)
  4. extractionExtract the aqueous layer with CH2Cl2 (3×100 mL)
  5. dry with materialCombine the organic layers, dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-98e6ab0732bd4e16bbd75fdceff59616
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

Loading…