Trifluoroacetic acid → HCID 58683903, compound

HRID 2079414Notes

Reaction equation

HRID 2079414 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-5921a247559c407d9cf719ae390de0c2
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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