Hydrochloric Acid → benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylate

HRID 2249677Notes

Reaction equation

HRID 2249677 reaction equation
[CH3:1][CH:2]([CH3:28])[CH2:3][CH:4]=[CH:5][C@@H:6]1[CH2:10][C@@H:9]([O:11]C2CCCCO2)[CH2:8][N:7]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].Cl.C(Cl)(Cl)Cl.O>O1CCCC1>[OH:11][C@H:9]1[CH2:8][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C@H:6]([CH:5]=[CH:4][CH2:3][CH:2]([CH3:28])[CH3:1])[CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6212ChloroformHCID 86630053benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-pyrrolidinecarboxylate

Product 1

HCID 86630054benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylateYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 12 ml of tetrahydrofuran is dissolved 0.60 g of benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-pyrrolidinecarboxylate, to which is added 12 ml of 6 mol/L hydrochloric acid. The mixture thus obtained is stirred at ambient temperature for 2 hours. A mixture of chloroform and water is added to the reaction mixture, 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=2:1) to obtain 0.43 g of benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylate as a light yellow oily product.

Workup

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

Sources & evidence

ORD record
ord-10edb66359e64cf08090efcf4751bb29
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

Loading…