Sodium Azide → (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH2:16]OS(C)(=O)=O)[C@@H:13]([OH:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[N:23]([CH2:16][C@@H:14]1[C@@H:13]([OH:22])[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:15]1)=[N+:24]=[N-:25]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
(3R,4R)-1-Benzyloxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine (125 mg) was then dissolved in N,N-dimethylformamide (3 mL) and sodium azide (50.0 mg) was added. The mixture was stirred at 100° C. for 1 hour and was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (5 mL). The solution was then washed with water (2×1 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The 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 (91.0 mg). This compound was identical to the compound obtained by Process A.
Workup
- concentrationwas concentrated under reduced pressure
- dissolutionThe resulting residue was dissolved in ethyl acetate (5 mL)
- washThe solution was then washed with water (2×1 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluant: ethyl acetate)
Sources & evidence
- ORD record
- ord-d636fbd4ffb7468bb5d52fd8c8e156de
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514451B2
Reaction notes
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