Sodium Chloride → 1-(2-Propen-1-yl) (2S)-1,2-pyrrolidinedicarboxylate

HRID 1650304Notes

Reaction equation

HRID 1650304 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1)([OH:3])=[O:2].Cl[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11].[OH-].[Na+].[Cl-].[Na+]>O.O1CCCC1.C(OCC)(=O)C>[CH2:13]([O:12][C:10]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[C:1]([OH:3])=[O:2])=[O:11])[CH:14]=[CH2:15]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 145742L-Proline

Product 1

HCID 109434831-(2-Propen-1-yl) (2S)-1,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (2S)-2-carboxypyrrolidine (40 g) in a mixture of water (200 ml) and tetrahydrofuran (200 ml) was added a solution of allyl chloroformate (44 ml) in tetrahydrofuran (40 ml) at ° C. while adjusting pH to around 9 with 4N aqueous sodium hydroxide. After stirring at ° C. for 1 hour at pH 9, the aqueous layer was saturated with sodium chloride, and the mixture was diluted with ethyl acetate (200 ml). The aqueous layer was separated and washed with ethyl acetate. After adjusting pH to around 2 with 6N hydrochloric acid, the mixture was extracted with two portions of ethyl acetate (200 ml×2). The combined extract was dried over magnesium sulfate and evaporated in vacuo to give (2S)-1-allyloxycarbonyl-2-carboxypyrrolidine (72.49 g).

Workup

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate
  3. extractionthe mixture was extracted with two portions of ethyl acetate (200 ml×2)
  4. extractionThe combined extract
  5. dry with materialwas dried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-81bb6efc94af47e0a56f2fe7a911fb50
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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