Hydrochloric Acid → HCID 54566831, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- temperaturecooling for 10 minutes
- temperatureTo the reaction mixture cooled at 0° C.
- customThe resulting precipitates
- filtrationwere filtered off
- customthe filtrate was evaporated in vacuo
- customto give a residue
- dry with materialthe solution was dried over anhydrous magnesium sulfate
- customevaporated in vacuo
- customto give a residue
- washThe residue was washed with n-hexane
- customdried in vacuo
Sources & evidence
- ORD record
- ord-9cfe794c2bce45c6b90a4032ea7dd3a2
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05608056
Reaction notes
Loading…