Tetrabutylammonium Fluoride → (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine
Reaction equation
[N:1]([CH2:4][C@@H:5]1[C@@H:9]([O:10][Si](C(C)(C)C)(C)C)[CH2:8][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:6]1)=[N+:2]=[N-:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[N:1]([CH2:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:6]1)=[N+:2]=[N-:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
(3R,4R)-3-Azidomethyl-1-benzyloxycarbonyl-4-- (tert-butyldimethylsilyl)oxypyrrolidine (3.05 g) was dissolved in tetrahydrofuran (50 mL). While this solution was chilled in an ice water bath, tetrabutylammonium fluoride (1 mol/L tetrahydrofuran solution, 13.3 mL) was added dropwise and the mixture was stirred for 1 hour, followed by addition of saturated brine (70 mL) and the mixture was extracted with ethyl acetate (150 mL, 100 mL). The ethyl acetate layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate) to give (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a milky white syrup (2.01 g).
Workup
- temperatureWhile this solution was chilled in an ice water bath
- extractionthe mixture was extracted with ethyl acetate (150 mL, 100 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate)
Sources & evidence
- ORD record
- ord-0c3751644fde4d0a910861235bc19108
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514451B2
Reaction notes
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