Triethylamine → (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1.C(N(CC)CC)C.Cl[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21]Participants
5
Conditions
- Temperature
- -5 °C
Procedure
A mixture of L-hydroxyproline methyl ester hydrochloride (the compound obtained in Reference Example 1-1); 24.37 g, 134 mmol) and triethylamine (41.2 ml, 295 mmol) in methylene chloride (240 ml) was stirred at room temperature for 10 minutes, cooled to -5° C., treated dropwise with a solution of allyl chloroformate (14.9 ml, 140 mmol) in methylene chloride (30 ml). The reaction mixture was stirred at -5° C. for 1 hour, and washed twice with water. The organic layer was dried over anhydrous sodium sulfate and evaporated to afford the title compound (30.8 g, 100% yield) as an oil.
Workup
- customobtained in Reference Example 1-1)
- washwashed twice with water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-bd5bf12fd1264bc7b28e30bb408c1419
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05095013
Reaction notes
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