Methyl vinyl ketone → HCID 23091639, compound

HRID 272851Notes

Reaction equation

HRID 272851 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][C:7]([CH:9]=[CH2:10])=[O:8].[BH4-].[Na+]>C1COCC1>[N:1]1([CH2:10][CH2:9][CH:7]([OH:8])[CH3:6])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 31268PyrrolidineHCID 4311764Sodium borohydride

Product 1

HCID 23091639HCID 23091639, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidine (2 ml, 24 mmol), THF (20 ml) and methyl vinylketone (2.5 ml, 31 mmol) were mixed together and stirred overnight. NaBH4 (1.17 g, 31 mmol) was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with water (20 ml) and extracted with TBME (2×20 ml). The combined organic extracts were dried over MgSO4, filtered, washed with TBME and concentrated in vacuo. The crude product was purified by column chromatography, eluting with DCM:MeOH:NH3 (94:5:1), to give the title compound as a pale yellow oil (1.3 g, 38%).

Workup

  1. stirringstirred for 3 hours
  2. customThe reaction was quenched with water (20 ml)
  3. extractionextracted with TBME (2×20 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. washwashed with TBME
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. washeluting with DCM:MeOH:NH3 (94:5:1)

Sources & evidence

ORD record
ord-09d29b9baae94b8db2e12820c9e23f93
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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