Sodium Azide → HCID 86600237, compound
Reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([CH2:13]OS(C)(=O)=O)[C@@H:10]([OH:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:13][C@@H:11]1[C@@H:10]([OH:19])[CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12]1)=[N+:21]=[N-:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
(3R,4R)-1-Benzyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine (835 mg), sodium azide (381 mg), and N,N-dimethylformamide (12 mL) were mixed with one another and the mixture was stirred at 120° C. for 1 hour. Subsequently, the reaction mixture was concentrated under reduced pressure. To the resulting residue, water (10 mL) was added and the mixture was extracted with diethyl ether (2×30 mL). The diethyl ether extracts were combined and the combined extract was dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate: methanol=20:1) to give 576 mg of (3R,4R)-3-azidomethyl-1-benzyl-4-hydroxypyrrolidine as a pale brown oil.
Workup
- concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
- additionTo the resulting residue, water (10 mL) was added
- extractionthe mixture was extracted with diethyl ether (2×30 mL)
- extractionthe combined extract
- dry with materialwas dried over anhydrous sodium sulfate
- concentrationwas concentrated under reduced pressure
- customThe resulting residue was purified on a silica gel column (eluant=ethyl acetate: methanol=20:1)
Sources & evidence
- ORD record
- ord-fe5118d282ee4bb797fb4c82d932b075
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153851B2
Reaction notes
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