Hydrochloric Acid → (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine

HRID 975647Notes

Reaction equation

HRID 975647 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][CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:6])[CH:2]=[CH2:3].Cl.C[O-].[Na+].CO.C(Cl)(Cl)Cl>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][CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 23694274Sodium methanolate methanolHCID 54510818(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine

Product 1

HCID 54134400(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidineYield 118.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine (11.11 g) in methanol (110 ml) was added conc. hydrochloric acid (7.32 ml) at ambient temperature with stirring and the solution was stirred at the same temperature for 2 hours. To a reaction solution was added 28% sodium methoxide-methanol solution (16.89 ml) under ice-cooling with stirring and the resulting insoluble material was filtered off. The filtrate was evaporated in vacuo to give a residue. To the residue was added chloroform. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to give crude (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine (9.19 g).

Workup

  1. stirringthe solution was stirred at the same temperature for 2 hours
  2. temperaturecooling
  3. stirringwith stirring
  4. filtrationthe resulting insoluble material was filtered off
  5. customThe filtrate was evaporated in vacuo
  6. customto give a residue
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-96c6739dafe340508cd0a5631c755766
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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