Hydrochloric Acid → Benzyl(3S,4S)-3-(Allyloxy)-4-aminopyrrolidine-1-carboxylate
Reaction equation
[CH2:1]([O:4][CH:5]1[CH:9]([NH:10]C(OC(C)(C)C)=O)[CH2:8][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:6]1)[CH:2]=[CH2:3].Cl.CO.CCOC(C)=O>C1COCC1.O1CCOCC1.C([O-])(O)=O.[Na+]>[CH2:1]([O:4][C@@H:5]1[C@@H:9]([NH2:10])[CH2:8][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:6]1)[CH:2]=[CH2:3]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 21.3 g (56.6 mmol) of benzyl 3-(allyloxy)-4-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate in 125 mL of THF was added 250 mL of 4 N HCl in dioxane solution. The reaction mixture was stirred at room temperature for 2 h, concentrated under reduced pressure to give an oil residue. This residue was redissolved in 200 mL of saturated NaHCO3 aqueous solution. The mixture was adjusted to pH 7-8, then was extracted with ethyl acetate twice (100 mL×2). The combined extracts were washed with brine, dried over Na2SO4, evaporated under reduced pressure to give an oil residue. Chromatography on silica gel column with 5% MeOH-EtOAc provided the title compound (10.5 g, 68%). MS (M+H)+ 277.
Workup
- concentrationconcentrated under reduced pressure
- customto give an oil residue
- extractionwas extracted with ethyl acetate twice (100 mL×2)
- washThe combined extracts were washed with brine
- dry with materialdried over Na2SO4
- customevaporated under reduced pressure
- customto give an oil residue
Sources & evidence
- ORD record
- ord-a52087fbf7b24481a4553d2a1b7f5dc5
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985730B2
Reaction notes
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