Hydrochloric Acid → (2S,4R)-4-hydroxy-N,N-dimethylpyrrolidine-2-carboxamide hydrochloride

HRID 1662684Notes

Reaction equation

HRID 1662684 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1C(OC(C)(C)C)=O)=[O:4].[ClH:19]>CCOC(C)=O>[ClH:19].[OH:10][C@H:8]1[CH2:7][NH:6][C@H:5]([C:3]([N:2]([CH3:18])[CH3:1])=[O:4])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25180889(2S,4R)-tert-butyl 2-(dimethylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 23535508(2S,4R)-4-hydroxy-N,N-dimethylpyrrolidine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 11.0 g of the compound obtained in Step 88-1 in EtOAc (100 ml) was added dropwise a solution of 4 mol/l hydrochloric acid in EtOAc (100 ml) over 20 minutes. The solution was stirred at room temperature for two hours and then the solvent was evaporated under reduced pressure. EtOAc was added, and the solution was stirred for 30 minutes. Thereafter, the precipitated solid was filtered and then dried to obtain 8.21 g of the title compound (colorless solid).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionEtOAc was added
  3. stirringthe solution was stirred for 30 minutes
  4. filtrationThereafter, the precipitated solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-2acaf965bcff49daa4c1497e3f458349
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

Loading…