Hydrochloric Acid → HCID 54567783, compound

HRID 975686Notes

Reaction equation

HRID 975686 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH2:20][C:21]#[N:22])=[O:6])[CH:2]=[CH2:3].Cl.C[O-].[Na+]>CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:20][C:21]#[N:22])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 53770963HCID 53770963, compound

Product 1

HCID 54567783HCID 54567783, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of (2R, 4R) -1-allyloxycarbonyl-2-cyanomethyl-4-t-butyldimethylsilyloxypyrrolidine (4.65 g) in methanol (23.3 ml) was added conc. hydrochloric acid (2.38 ml) at ice-cooling. After stirring at 15°-25° C. for 1 hour, the solution was cooled at 5° C. 28% Sodium methoxide in methanol (5.52 ml) was added to the cold solution and the mixture was stirred at 0°-10° C. for 10 minutes. After removal of insoluble material by filtration, the filtrate was concentrated under reduced pressure. Acetonitrile (23.3 ml) was added to the residue and the solution was evaporated. The residue was washed with n-hexane (20 ml) five times and evaporated to give (2R,4R)-1-allyloxycarbonyl-2-cyanomethyl-4-hydroxypyrrolidine (2.99 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 0°-10° C. for 10 minutes
  3. customAfter removal of insoluble material
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionAcetonitrile (23.3 ml) was added to the residue
  7. customthe solution was evaporated
  8. washThe residue was washed with n-hexane (20 ml) five times
  9. customevaporated

Sources & evidence

ORD record
ord-bfbf59bea912430e8d7c08a271e5fc4f
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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