Perfluorooctanesulfonyl fluoride → (3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine
Reaction equation
[N:1]([CH2:4][C@@H:5]1[C@@H:9](O)[CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=[N+:2]=[N-:3].N12CCCN=C1CCCCC2.[F:32]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>C1(C)C=CC=CC=1>[N:1]([CH2:4][C@@H:5]1[C@H:9]([F:32])[CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=[N+:2]=[N-:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Process (B): (3R,4R)-3-Azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine (1.79 g) was dissolved in toluene (56 mL). While this solution was cooled on an ice bath, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.03 mL) was added. This was followed by dropwise addition of perfluoro-1-octanesulfonyl fluoride (2.80 mL) and stirring for another 1 hour. Insoluble materials were removed from the reaction mixture by filtration and were washed with toluene. The filtrate and the washing solution were combined and the combined organic layer was concentrated under reduced pressure. The resulting residue was then purified on a silica gel column (eluant=hexane:ethyl acetate=2:1) to give 1.58 g of (3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine as a pale brown syrup-like product. The compound was identical to the compound obtained by Process (A).
Workup
- temperatureWhile this solution was cooled on an ice bath
- customInsoluble materials were removed from the reaction mixture by filtration
- washwere washed with toluene
- concentrationthe combined organic layer was concentrated under reduced pressure
- customThe resulting residue was then purified on a silica gel column (eluant=hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-7d6dc5104ba0430dbd9c413a89d43caa
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153851B2
Reaction notes
Loading…