Pyridine, hydrofluoride (1:1) → HCID 67491014, compound
Reaction equation
N1C=CC=CC=1.F.[CH3:8][O:9][C:10]([CH:12]1[CH:16]([C@H:17]([CH3:27])[CH2:18][O:19][Si](C(C)(C)C)(C)C)[CH2:15][N:14]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:13]1)=[O:11]>N1C=CC=CC=1>[CH3:8][O:9][C:10]([CH:12]1[CH:16]([C@H:17]([CH3:27])[CH2:18][OH:19])[CH2:15][N:14]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:13]1)=[O:11]Participants
Procedure
Hydrogen fluoride-pyridine (2 mL) was added to a solution of 4-[(S)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (6.0 g, 7.1 mmol) in pyridine (20 mL) under ice-cooling, and the mixture was stirred at room temperature for 13 hours. Further 2 mL of hydrogen fluoride-pyridine was added, and the mixture was stirred for 23 hours. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate and washing with 1N hydrochloric acid and brine. After drying over magnesium sulfate and filtration, the solvent was evaporated under reduced pressure to give 4.5 g (quantitative) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.
Workup
- temperaturecooling
- stirringthe mixture was stirred for 23 hours
- extractionfollowed by extraction with ethyl acetate
- washwashing with 1N hydrochloric acid and brine
- dry with materialAfter drying over magnesium sulfate and filtration
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-2f1f997c19e94d5c9e35cada9308c34d
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618094B2
Reaction notes
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