Hydrochloric Acid → 2-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)-

HRID 220744Notes

Reaction equation

HRID 220744 reaction equation
[F:1][C@@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([NH2:9])=[O:8])[CH2:3]1.[ClH:10]>C(O)(C)C.CCOCC>[ClH:10].[F:1][C@@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([NH2:9])=[O:8])[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12066286(2S,4S)-4-Fluoropyrrolidine-2-carboxamide

Product 1

HCID 451589172-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)-Yield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

(2S,4S)-4-Fluoropyrrolidine-2-carboxamide (119 mg, 0.9 mmol) obtained in step 1 was dissolved in 5 ml of isopropanol. Into the solution, 1.5 mL (HCl 1.5 mmol) of 1.0 M HCl in ether was added, and after the mixture was stirred for 10 minutes, all the volatiles were removed. The resulting solid was dried in vacuum at 50° C. for 2 h, giving 148 mg (yield 98%) of (2S,4S)-4-fluoropyrrolidine-2-carboxamide hydrochloride (Ga). The product was identified by comparison with an authentic sample.

Workup

  1. customall the volatiles were removed
  2. customThe resulting solid was dried in vacuum at 50° C. for 2 h

Sources & evidence

ORD record
ord-88abaa587d6843d2821d7429a2ca88be
Source dataset
uspto-grants-2012_06
Patent number
US08203003B2

Reaction notes

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