Triethylamine → (2S)-1-azido-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol
Reaction equation
[N+](C1C=C(S(O[CH2:14][C@H:15]2[CH2:17][O:16]2)(=O)=O)C=CC=1)([O-])=O.C(N(CC)CC)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][C:38]=1[Cl:39])[O:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[N-:40]=[N+:41]=[N-:42].[Na+]>CN(C=O)C>[N:40]([CH2:17][C@@H:15]([OH:16])[CH2:14][N:33]1[CH2:34][CH2:35][CH:30]([O:29][C:28]2[CH:36]=[CH:37][C:38]([Cl:39])=[C:26]([Cl:25])[CH:27]=2)[CH2:31][CH2:32]1)=[N+:41]=[N-:42]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
(2R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate (21.1 g, 81.3 mmol) in DMF (300 ml) was treated with triethylamine (22.6 ml, 163.0 mmol) followed by 4-(3,4-dichlorophenoxy)-piperidine (20 g, 81.3 mmol). The mixture was stirred overnight at 60° C. Sodium azide (16 g, 243.9 mmol) was added to the mixture and the reaction was stirred for a further 72 h. The solution was carefully concentrated under vacuum and the residue was diluted with water (600 ml), extracted with ethyl acetate (1500 ml). The organic layer was washed twice with water (500 ml), then brine (200 ml) and concentrated under vacuum to afford an oil.
Workup
- stirringthe reaction was stirred for a further 72 h
- concentrationThe solution was carefully concentrated under vacuum
- additionthe residue was diluted with water (600 ml)
- extractionextracted with ethyl acetate (1500 ml)
- washThe organic layer was washed twice with water (500 ml)
- concentrationbrine (200 ml) and concentrated under vacuum
- customto afford an oil
Sources & evidence
- ORD record
- ord-50c0131af8e84877ba9f5c46efbe54e8
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709500B2
Reaction notes
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