Hydrochloric Acid → (S)-Pyrrolidine-2-carboxamide monohydrochloride

HRID 2364832Notes

Reaction equation

HRID 2364832 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1C(OC(C)(C)C)=O)(=[O:3])[NH2:2].[ClH:16].O1CCOCC1>>[ClH:16].[NH:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:1]([NH2:2])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 7019053tert-butyl (S)-2-carbamoylpyrrolidine-1-carboxylate

Product 1

HCID 12707183(S)-Pyrrolidine-2-carboxamide monohydrochlorideYield 104%

Procedure

To (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (29.8 g, 139 mmol) was added a solution of 4N HCl in dioxane (209 mL, 836 mmol) and the resultant mixture stirred at room temperature for 18 hrs. The mixture was then concentrated and triturated with diethyl ether then vacuum filtered and dried under vacuum to provide 21.6 g (104%) of the title product as a colorless solid.

Workup

  1. concentrationThe mixture was then concentrated
  2. customtriturated with diethyl ether
  3. filtrationvacuum filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f1fe8a4e364e4bf3beb2d87b2d85b83e
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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