Water → benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-[(2-methyl-2-propenyl)oxy]-1-pyrrolidinecarboxylate

HRID 2249678Notes

Reaction equation

HRID 2249678 reaction equation
[OH-].[Na+].[OH:3][C@H:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C@H:6]([CH:19]=[CH:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:5]1.Cl[CH2:26][C:27]([CH3:29])=[CH2:28].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:23][CH:22]([CH3:24])[CH2:21][CH:20]=[CH:19][C@@H:6]1[CH2:5][C@@H:4]([O:3][CH2:28][C:27]([CH3:29])=[CH2:26])[CH2:8][N:7]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 14798Sodium HydroxideHCID 86630054benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylate

Product 1

HCID 86630055benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-[(2-methyl-2-propenyl)oxy]-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

After adding 0.04 g of tetrabutylammonium bromide to 8 ml of 50% aqueous solution of sodium hydroxide, the mixture is heated to 120° C. Thereto is dropwise added a solution of 0.40 g of benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylate and 0.65 ml of 3-chloro-2-methyl-1-propene in 0.8 ml of toluene over a period of 5 minutes. The mixture thus obtained is heated under reflux for 30 minutes with stirring. The reaction mixture is cooled to ambient temperature, toluene and water are added, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=10:1) to obtain 0.31 g of benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-[(2-methyl-2-propenyl)oxy]-1-pyrrolidinecarboxylate as a colorless oily product.

Workup

  1. customThe mixture thus obtained
  2. temperatureis heated
  3. temperatureunder reflux for 30 minutes
  4. temperatureThe reaction mixture is cooled to ambient temperature
  5. customthe organic layer is separated
  6. customThe organic layer thus obtained
  7. washis washed with water and saturated aqueous solution of sodium chloride successively
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off under reduced pressure
  10. customThe residue thus obtained
  11. customis purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-cbc969d85a374ad697dcc5e6833b690d
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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