2,2,6,6-Tetramethylpiperidine → HCID 90310646, compound
Reaction equation
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[C:16]([Si:20]([O:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=1[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].[B:37](OC(C)C)([O:42]C(C)C)[O:38]C(C)C>C1COCC1>[Si:20]([O:23][C:24]1[C:29]([F:30])=[C:28]([B:37]([OH:42])[OH:38])[CH:27]=[CH:26][C:25]=1[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:22])[CH3:21]Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution consisting of 2,2,6,6-tetramethylpiperidine (0.50 mL, 3.0 mmol) and dry THF (2 mL) was cooled to −78° C. and treated with n-butyllithium (1.1 mL, 2.75 mmol, 2.5 M in hexanes). After stirring for 5 minutes, the reaction was warmed to rt for 5 minutes before cooling back down to −78° C. The reaction was then treated with tert-butyl(2-cyclohexyl-6-fluorophenoxy)dimethylsilane (0.719 g, 2.33 mmol) and triisopropyl borate (0.60 mL, 2.6 mmol) and stirred for 5 minutes. The reaction mixture was warmed to rt, quenched with saturated NH4Cl (2 mL), and extracted with EtOAc (2×5 mL). The combined organic extracts were washed with brine (3×5 mL), dried over MgSO4, filtered, and concentrated to dryness to yield the title compound (0.833 g, 101%), which was used without purification.
Workup
- temperaturethe reaction was warmed to rt for 5 minutes
- temperaturebefore cooling back down to −78° C
- stirringstirred for 5 minutes
- temperatureThe reaction mixture was warmed to rt
- customquenched with saturated NH4Cl (2 mL)
- extractionextracted with EtOAc (2×5 mL)
- washThe combined organic extracts were washed with brine (3×5 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-f4ecf06e4d294929abe0b3b9d4100af3
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073876B2
Reaction notes
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