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

HRID 1411377Notes

Reaction equation

HRID 1411377 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 4 N HCl in dioxane (209 mL, 836 mmol), and the resultant mixture was stirred at room temperature for 18 hours. 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-1aed09e966cd464abcd94f01f8032aa1
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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