Trifluoroacetic acid → 5-pyrrolidin-1-ylmethyl-2,3-dihydro-1H-isoindole

HRID 624166Notes

Reaction equation

HRID 624166 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:18]1([CH2:17][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][NH:8][CH2:16]3)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68751282HCID 68751282, compound

Product 1

HCID 687507855-pyrrolidin-1-ylmethyl-2,3-dihydro-1H-isoindole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.90 g 5-pyrrolidin-1-ylmethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (raw material; 4.96 mmol) in 5 ml dichloromethane was added 3.82 ml trifluoroacetic acid (49.6 mmol) and the reaction mixture was stirred at room temperature overnight. The trifluoroacetic acid and dichloromethane were evaporated under reduced pressure, water was added to the residue, the acidic aqueous phase extracted two times with ethyl acetate, the aqueous phase was basified with diluted NaOH and then subsequently extracted three times with dichloromethane. The dichloromethane phase was washed once with brine, dried over Na2SO4, filtered, and the solvent was removed under vacuum. The title compound was used without further purification in the next step. LCMS: m/z 203.2 (M+H).

Workup

  1. customThe trifluoroacetic acid and dichloromethane were evaporated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe acidic aqueous phase extracted two times with ethyl acetate
  4. extractionsubsequently extracted three times with dichloromethane
  5. washThe dichloromethane phase was washed once with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under vacuum
  9. customThe title compound was used without further purification in the next step

Sources & evidence

ORD record
ord-59cac2097efb4bcf947117e8d14067ae
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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