HCID 68027201, compound → HCID 66765572, compound

HRID 527913Notes

Reaction equation

HRID 527913 reaction equation
[CH3:1][N:2]([C@@H:15]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1)[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([F:13])([F:12])[F:11]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][N:2]([C@@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([F:13])([F:11])[F:12]

Participants

4

Reactant 1

HCID 68027201HCID 68027201, compound

Product 1

HCID 66765572HCID 66765572, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-tert-butyl 3-(N-methyl-2-(trifluoromethyl)benzamido)pyrrolidine-1-carboxylate (1 mmol) in TFA (2 mL) and DCM (2 mL) was stirred at room temperature for 2 hours, concentrated and diluted with water. It was then basified with aqueous NaHCO3 solution till pH=˜9, and extracted with EtOAc. The combined extracts were dried, filtered, and concentrated to give (R)—N-methyl-N-(pyrrolidin-3-yl)-2-(trifluoromethyl)benzamide.

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9dfc06220b07429a81adb33535196ba6
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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