Hydrochloric Acid → HCID 86650481, compound
Reaction equation
[Li]CCCC.[CH3:6][C:7](=[N:9][OH:10])[CH3:8].C[O:12][C:13]([C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.Cl>C1COCC1>[CH2:20]([N:16]1[CH2:17][CH2:18][CH2:19][C@H:15]1[C:13](=[O:12])[CH2:6][C:7](=[N:9][OH:10])[CH3:8])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 12.5 ml BuLi (1.6 M in hexane) was added a solution of 0.73 g acetone oxime in 8 ml THF at 0° C. After 30 minutes a solution of 1.0 g (S)-1-Benzyl-pyrrolidine-2-carboxylic acid methyl ester in 5 ml THF was added dropwise over a period of 20 minutes at this temperature. The resulting suspension was stirred for another 3 h at 0° C. before being cannulated into 21 ml 3 M HCl. The phases were separated; the aqueous phase was brought to pH8 using solid NaHCO3 and extracted with dichloromethane (3×) to give the crude product. Yield: 1.3 g mixture of E/Z isomers.
Workup
- customThe phases were separated
- extractionextracted with dichloromethane (3×)
Sources & evidence
- ORD record
- ord-0b3efde91e1e4e7a9a77c50accca8b51
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426420B2
Reaction notes
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