Triethylamine → HCID 52324471, compound
Reaction equation
[F:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[F:1][C@H:2]1[C@H:7]([O:8][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate (52.76 g, 241 mmol) dissolved in anhydrous methylene chloride (1 L) was cooled to 0° C. and treated with triethylamine (43.6 mL, 313 mmol) followed by methanesulfonyl chloride (20.5 mL, 265 mmol). The solution was allowed to warm slowly to ambient temperature and stirred for 14 hours. The mixture was partitioned between saturated NaHCO3 (400 mL) and methylene chloride (400 mL). The aqueous layer was extracted with methylene chloride. The combined organic phases were washed with 1N HCl and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with hexanes:EtOAc to provide the desired product (7.24 g).
Workup
- temperatureto warm slowly to ambient temperature
- customThe mixture was partitioned between saturated NaHCO3 (400 mL) and methylene chloride (400 mL)
- extractionThe aqueous layer was extracted with methylene chloride
- washThe combined organic phases were washed with 1N HCl and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting with hexanes
Sources & evidence
- ORD record
- ord-7681f7a066a9433189d0a7110e900d83
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138181B2
Reaction notes
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