Hydrochloric Acid → HCID 53832192, compound

HRID 975639Notes

Reaction equation

HRID 975639 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][CH2:22][N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=[O:6])[CH:2]=[CH2:3].Cl>C(#N)C>[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][CH2:22][N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53934734HCID 53934734, compound

Product 1

HCID 53832192HCID 53832192, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-[3-(imidazol-1-yl)propyl]pyrrolidine (19.0 g) in acetonitrile (94 ml) was added conc. hydrochloric acid (9.4 ml) dropwise at 0° C. The solution was stirred at the same temperature for 30 minutes and quenched by the addition of triethylamine (16.7 ml). To the mixture was added ethyl acetate (200 ml) and the insoluble solid was removed by filtration. The filtrate was concentrated and the residue was dissolved in ethyl acetate (100 ml). The insoluble solid was filtered off and the filtrate was concentrated to give a light brown paste. The paste was chromatographed on a 90 g of silica gel to give (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-[3-(imidazol-1-yl)propyl]pyrrolidine (12.5 g) as a pale yellow paste.

Workup

  1. customquenched by the addition of triethylamine (16.7 ml)
  2. additionTo the mixture was added ethyl acetate (200 ml)
  3. customthe insoluble solid was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  6. filtrationThe insoluble solid was filtered off
  7. concentrationthe filtrate was concentrated
  8. customto give a light brown paste
  9. customThe paste was chromatographed on a 90 g of silica gel

Sources & evidence

ORD record
ord-6403da31dd5e459788e55b546056c9c5
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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