2,2,6,6-Tetramethylpiperidine → HCID 178418821, compound
Reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[NH:3]1.C([Li:15])CCC>O1CCCC1>[Li:15][N:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]1([CH3:10])[CH3:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To 2 ml of tetrahydrofuran, 0.09 ml (0.52 mmol) of 2,2,6,6-tetramethylpiperidine was added. It was then cooled to -70° C., and n-butyl lithium (0.52 mmol) was added thereto in the presence of an argon flow to obtain lithium 2,2,6,6-tetramethylpiperidide solution. Separately, 100 mg (0.24 mmol) of 1-[(2-t-butyldimethylsilyloxyethoxy)methyl]-2-thio-6-phenyluracil was dissolved in 2 ml tetrahydrofuran, and the resulting solution was added dropwise to the above lithium 2,2,6,6-tetramethylpiperidide solution and allowed to react at -70° C. for 1 hour. To this reaction solution, 0.07 ml (1.2 mmol) of methyl iodide was added and allowed to react for 1 hour. Then, after subjected to the same treatment as in Example 1 (1). the resultant was reacted and treated in the same manner as in Example 1 (2). The residue was crystallized from toluene to obtain 39 mg of the target compound (Yield: 60%).
Sources & evidence
- ORD record
- ord-b49b0358f39041cfbe439678f5c3c15d
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112835
Reaction notes
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