Hydrogen chloride-ethyl acetate → 2-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)-

HRID 1180118Notes

Reaction equation

HRID 1180118 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[C:14](=[O:16])[NH2:15])=O)(C)(C)C.[ClH:17].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:17].[C:14]([C@@H:9]1[CH2:10][C@H:11]([F:13])[CH2:12][NH:8]1)(=[O:16])[NH2:15]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 497605222-Methyl-2-propanyl (2S,4S)-2-carbamoyl-4-fluoro-1-pyrrolidinecarboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(2S,4S)-1-(tert-Butoxycarbonyl)-2-carbamoyl-4-fluoropyrrolidine (122 g) was suspended in ethyl acetate (400 mL). While stirring this suspension under ice cooling, 4 mol/L hydrochloric acid-ethyl acetate (525 mL) was slowly added dropwise. After stirring at ice-cold temperature for 30 minutes and at room temperature for 3 hours, the precipitated crystal was collected by filtration to give the titled compound (85.9 g, white powder).

Workup

  1. stirringAfter stirring at ice-cold temperature for 30 minutes and at room temperature for 3 hours
  2. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-3e944c80b04642b98d04a2ecf5308ad8
Source dataset
uspto-grants-2007_10
Patent number
US07279584B2

Reaction notes

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