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

HRID 1429198Notes

Reaction equation

HRID 1429198 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-759b2798a8304ca88c2341c3d33ca656
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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