Triethylamine → D-threo-Pentitol, 1,5-anhydro-2,4-dideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 3-methanesulfonate
Reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][O:5][CH2:4][C@H:3]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.O>[CH3:23][S:24]([O:1][C@@H:2]1[CH2:7][CH2:6][O:5][CH2:4][C@H:3]1[NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:15])(=[O:26])=[O:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Tert-butyl ((3R,4R)-4-hydroxytetrahydro-2H-pyran-3-yl)carbamate (1.6 g, 7.36 mmol) was taken up in CH2Cl2 (20 ml) and cooled to 0° C. followed by addition of Et3N (1.232 ml, 8.84 mmol). After 5 minutes methanesulfonyl chloride (0.631 ml, 8.10 mmol) in DCM (5 ml) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes and allowed to warm to ambient temperature while stirring for 2 hours. The reaction mixture was diluted with water and DCM and the layers were separated. The organic layers were combined and washed with water twice, dried over Na2SO4, and the solvent removed in vacuo. The residue was dried under high vacuum overnight to afford recovered (3R,4R)-3-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-4-yl methanesulfonate (2.2 g, 7.45 mmol, 100% yield) as a white solid.
Workup
- temperatureto warm to ambient temperature
- stirringwhile stirring for 2 hours
- customthe layers were separated
- washwashed with water twice
- dry with materialdried over Na2SO4
- customthe solvent removed in vacuo
- customThe residue was dried under high vacuum overnight
- customto afford
Sources & evidence
- ORD record
- ord-5d7973ea60a34c9ebbfe1eea0c859deb
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434700B2
Reaction notes
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