Hydrochloric Acid → (R)-4,4-difluoro-2-(3-fluorophenyl)pyrrolidine

HRID 63987Notes

Reaction equation

HRID 63987 reaction equation
[F:1][C:2]1([F:21])[CH2:6][N:5](C(OC(C)(C)C)=O)[C@@H:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH2:3]1.Cl.[OH-].[Na+]>>[F:21][C:2]1([F:1])[CH2:6][NH:5][C@@H:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66684270(R)-tert-butyl 4,4-difluoro-2-(3-fluorophenyl)pyrrolidine-1-carboxylate

Product 1

HCID 66684260(R)-4,4-difluoro-2-(3-fluorophenyl)pyrrolidine

Conditions

Temperature
60 °C

Procedure

To (R)-tert-butyl 4,4-difluoro-2-(3-fluorophenyl)pyrrolidine-1-carboxylate (180 mg, 0.6 mmol) in a pressure reaction tube was added a solution of HCl (2 mL, 4 N dioxane, 8 mmol), then the reaction was sealed and heated at 60° C. for 4 hours. For workup, the reaction was poured into a mixture of ice and 1 M NaOH, and extracted with several portions of EtOAc. The combined organic extracts were filtered through a Phase Separator filter paper and concentrated, yielding the final product as clear oil, which was used in the next step without further purification.

Workup

  1. customthe reaction was sealed
  2. extractionextracted with several portions of EtOAc
  3. filtrationThe combined organic extracts were filtered through a Phase Separator
  4. filtrationfilter paper
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-669d0e9dc1e646d88e437721c15b9960
Source dataset
uspto-grants-2016_09
Patent number
US09447104B2

Reaction notes

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