Trifluoroacetic acid → methyl (2S,5R)-5-(4-bromophenyl)pyrrolidine-2-carboxylate

HRID 2264825Notes

Reaction equation

HRID 2264825 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C@@H:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>[Pt]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[NH:12][C@H:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59596717methyl (2S)-5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Product 1

HCID 59596687methyl (2S,5R)-5-(4-bromophenyl)pyrrolidine-2-carboxylateYield 79.7%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst2×

Procedure

A solution of methyl (2S)-5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (D76, 799 mg, 2.83 mmol) and Pt/C (50 mg) was stirred under hydrogen (1 atm) overnight. Then TFA (0.25 ml) was added and hydrogenation was continued for another 2 h. Then more Pt/C (100 mg) was added and the mixture was stirred for additional 9 h under hydrogen (1 atm). After that additional catalyst (100 mg) and TFA (0.25 ml) was added and stirring was continued for another 5 h under hydrogen atmosphere. Then additional catalyst was added (100 mg). After additional 4 h the reaction was finished and the solution was filtered over celite, evaporated and purified using a SCX cartridge to afford the title compound (641 mg, 79%). UPLC: Rt 0.47 min; MS: (ES/+) m/z: 284, 286 [MH+], C12H14BrNO2 requires 284.

Workup

  1. stirringstirring
  2. waitwas continued for another 5 h under hydrogen atmosphere
  3. additionThen additional catalyst was added (100 mg)
  4. waitAfter additional 4 h the reaction was finished
  5. filtrationthe solution was filtered over celite
  6. customevaporated
  7. custompurified

Sources & evidence

ORD record
ord-8693b20e87cd4e89b8ea24749cf3d375
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

Loading…