Hydrochloric Acid → HCID 54566831, compound

HRID 975655Notes

Reaction equation

HRID 975655 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][OH:22])=[O:6])[CH:2]=[CH2:3].Cl.C[O-].[Na+]>CO.ClCCl>[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][OH:22])=[O:6])[CH:2]=[CH2:3]

Participants

6

Procedure

A solution of (2R,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(2-hydroxyethyl)pyrrolidine (5.0 g) and conc. hydrochloric acid (2.53 ml) in methanol (25 ml) was stirred under ice-cooling for 10 minutes and then stirred at ambient temperature for 1 hour. To the reaction mixture cooled at 0° C. was added 28% sodium methoxide in methanol solution (5.84 ml). The resulting precipitates were filtered off and the filtrate was evaporated in vacuo to give a residue. The residue was dissolved in dichloromethane (15 ml) and the solution was dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. The residue was washed with n-hexane and dried in vacuo to give (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-hydroxyethyl)pyrrolidine (3.10 g).

Workup

  1. temperaturecooling for 10 minutes
  2. temperatureTo the reaction mixture cooled at 0° C.
  3. customThe resulting precipitates
  4. filtrationwere filtered off
  5. customthe filtrate was evaporated in vacuo
  6. customto give a residue
  7. dry with materialthe solution was dried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a residue
  10. washThe residue was washed with n-hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-9cfe794c2bce45c6b90a4032ea7dd3a2
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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