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

HRID 1470991Notes

Reaction equation

HRID 1470991 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-21d156fea55d4e6396955523ce73d32a
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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