Sodium Chloride → tert-butyl (2S,4R)-4-hydroxy-2-(methylcarbamoyl)pyrrolidine-1-carboxylate

HRID 5071

Reaction equation

HRID 5071 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.[CH3:23][NH2:24].[Cl-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:16])[NH:24][CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6329MethylamineHCID 10928Ethyl chloroformateHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 10847882tert-butyl (2S,4R)-4-hydroxy-2-(methylcarbamoyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

9.91 ml of triethylamine were added at -40° C. to a solution of 15.03 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 250 ml of dry tetrahydrofuran, and then a solution of 6.81 ml of ethyl chloroformate in 30 ml of dry tetrahydrofuran was added at -30° to -40° C. to the resulting mixture, which was then stirred at the same temperature for 1 hour, 16.82 ml of a 40% by volume aqueous methylamine solution were then added at -30° C., and the temperature of the reaction mixture was allowed to rise to room temperature; the reaction was then allowed to continue for 1 hour. At the end of this time, the reaction mixture was mixed with a small amount of an aqueous solution of sodium chloride and extracted thrice with ethyl acetate. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, giving 12.76 g of the title compound as a colorless oil.

Workup

  1. customto rise to room temperature
  2. waitto continue for 1 hour
  3. extractionextracted thrice with ethyl acetate
  4. washThe combined extracts were washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4d674adf922840e691348acf82353519
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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