Propargyl bromide → HCID 57686375, compound

HRID 1038047

Reaction equation

HRID 1038047 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4].[Li+].[CH3:18][CH:19]([N-]C(C)C)[CH3:20].C(Br)C#C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([CH2:20][C:19]#[CH:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 2724682Lithium diisopropylamideHCID 45727751-Tert-butyl 3-methyl pyrrolidine-1,3-dicarboxylate

Product 1

HCID 57686375HCID 57686375, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 1 (6 mmol) was dissolved in THF (20 mL) and cooled down to −78° C. in a dry ice-acetone bath. LDA (5 mL, 2.0 M, 10 mmol) was then added dropwise. The mixture was stirred at −78° C. for 1 hr. Propargyl bromide (1.5 mL) was added in neat. The reaction was allowed to warm to rt naturally and stirred for 24 hrs. It was then quenched with sat. NH4Cl solution, extracted with ethyl acetate 2×50 mL. The organic layer was washed with brine, dried (MgSO4) and concentrated. The crude was purified on silica gel column using 4:1 hexanes/ethyl acetate to get the title compound (0.65 g) as an off-white gum. MS (267, M+H)

Workup

  1. temperatureto warm to rt naturally
  2. stirringstirred for 24 hrs
  3. customIt was then quenched with sat. NH4Cl solution
  4. extractionextracted with ethyl acetate 2×50 mL
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude was purified on silica gel column

Sources & evidence

ORD record
ord-958c55e717914987b3bb92a34f02a820
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Linked notes

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