Hydrochloric Acid → (2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidine

HRID 1090540Notes

Reaction equation

HRID 1090540 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](=[CH2:12])[CH2:9][C@H:8]1[CH2:13][O:14][Si](C(C)(C)C)(C)C)=[O:6])[CH:2]=[CH2:3].Cl.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](=[CH2:12])[CH2:9][C@H:8]1[CH2:13][OH:14])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 18639168(2S)-1-allyloxycarbonyl-2-(t-butyldimethylsilyloxymethyl)-4-methylenepyrrolidine

Product 1

HCID 57149333(2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidineYield 97.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (2S)-1-allyloxycarbonyl-2-(t-butyldimethylsilyloxymethyl)-4-methylenepyrrolidine (2.88 g) in ethyl acetate (100 ml) was added 6N hydrochloric acid (3.0 ml) at ambient temperature. After stirring for 1 hour at ambient temperature, to the mixture were added potassium carbonate (2.54 g) and brine (30 ml) with stirring. The organic layer was separated, washed in turn with aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (40 ml) eluting with a mixture of n-hexane and ethyl acetate (3:1 V/V) to give (2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidine (1.78 g).

Workup

  1. stirringwith stirring
  2. customThe organic layer was separated
  3. washwashed in turn with aqueous sodium hydrogen carbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (40 ml)
  7. washeluting with a mixture of n-hexane and ethyl acetate (3:1 V/V)

Sources & evidence

ORD record
ord-27574aa2f87f4c67869e37db7426cf59
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

Loading…