Trifluoroacetic acid → HCID 58683903, compound

HRID 2062330Notes

Reaction equation

HRID 2062330 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]1([C:11]([NH:13][C@@H:14]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)=[O:12])[CH2:10][CH2:9]1>C(Cl)Cl>[NH:16]1[CH2:17][CH2:18][C@@H:14]([NH:13][C:11]([CH:8]2[CH2:9][CH2:10]2)=[O:12])[CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 586838971,1-Dimethylethyl (3R)-3-[(cyclopropylcarbonyl)amino]-1-pyrrolidinecarboxylate

Product 1

HCID 58683903HCID 58683903, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of (R)-tert-butyl 3-(cyclopropanecarboxamido)pyrrolidine-1-carboxylate (500 mg, 1.96 mmol) in 5 mL CH2Cl2. After stirring for 30 min, the reaction was quenched with 1M NaOH solution till neutral and extracted twice with EtOAc. The organic extracts were combined, dried over MgSO4, filtered, and concentrated to yield N-((R)-pyrrolidin-3-yl)cyclopropanecarboxamide (250 mg) which was used without further purification. LC/MS: m/z 155.3 (M+H)+ at 0.6 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe reaction was quenched with 1M NaOH solution till neutral and
  2. extractionextracted twice with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1a4c78c0751f441da3b2a88915dd4ee0
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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