Acetic Acid → (2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carbonitrile
Reaction equation
[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:17])[CH2:8][O:9][Si](C(C)(C)C)(C)C)[C@H:4]([C:18]#[N:19])[CH2:3]1.O.C(O)(=O)C>O1CCCC1>[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:17])[CH2:8][OH:9])[C@H:4]([C:18]#[N:19])[CH2:3]1Participants
5
Conditions
- Temperature
- 50 °C
Procedure
(2S,4S)-4-fluoro-1-[2-(tert-butyldimethylsilyloxy)acetyl]pyrrolidine-2-carbonitrile (5.50 g) was dissolved in tetrahydrofuran (37 mL). To this solution, water (37 mL) and acetic acid (115 mL) were sequentially added and the mixture was stirred at 50° C. for 7.5 hours and then at 70° C. for 9 hours. Subsequently, the reaction mixture was concentrated under reduced pressure and the resulting pale brown tar-like residue was triturated with diethyl ether. The resulting solid was collected by filtration and dried under reduced pressure to give (2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carbonitrile as a pale brown solid (3.19 g).
Workup
- waitat 70° C. for 9 hours
- concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
- customthe resulting pale brown tar-like residue was triturated with diethyl ether
- filtrationThe resulting solid was collected by filtration
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-fa379d84b0304b3da7ee545f642da20c
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915427B2
Reaction notes
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