Sulfuric Acid → (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine

HRID 1090503Notes

Reaction equation

HRID 1090503 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[C:13]([OH:15])=[O:14])=[O:6])[CH:2]=[CH2:3].S(=O)(=O)(O)O.[CH2:21](N(CC)CC)C>CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[C:13]([O:15][CH3:21])=[O:14])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 18639171(2S,4R)-1-allyloxycarbonyl-2-carboxy-4-hydroxypyrrolidine

Product 1

HCID 10633157(2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-2-carboxy-4-hydroxypyrrolidine (426 g) in methanol (3 l) was added 36N sulfuric acid (45 ml) at 10° C., and the mixture was allowed to heat to reflux for 2 hours. After cooling to ambient temperature, to this mixture was added triethylamine (430 ml) and the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate (3 l) and the solution was washed with brine, dried over magnesium sulfate and evaporated to give (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine (385.6 g).

Workup

  1. temperatureto heat
  2. temperatureto reflux for 2 hours
  3. customthe mixture was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (3 l)
  5. washthe solution was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-13af2940014946ebbefd39e7e85015c1
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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