Hydrochloric Acid → HCID 19900248, compound

HRID 1029677Notes

Reaction equation

HRID 1029677 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([O:15]C2CCCCO2)[CH3:14])[CH:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([OH:15])[CH3:14])[CH:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15117327HCID 15117327, compound

Product 1

HCID 19900248HCID 19900248, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-t-butyloxycarbonyl-2-methyl-3-(1-tetrahydropyranyloxyethyl)pyrrolidine (10.2 g) in acetic acid (100 ml) was added 6N-hydrochloric acid solution (100 ml) at ambient temperature. After stirring for 12 hours, the solvent was evaporated. The residue was dissolved into a mixture of tetrahydrofuran (50 ml) and water (50 ml). To the solution was dropwise added allyl chloroformate (4.1 ml) at 0° C., while adjusting pH to 9~10 with 30% aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, and then the organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated to give 1-t-butyloxycarbonyl-3-(1-hydroxyethyl)-2-methylpyrrolidine 7.45 g).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved into a mixture of tetrahydrofuran (50 ml) and water (50 ml)
  3. customat 0° C.
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3cbd99f9dee64c5d97a170d70357c213
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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