2,6-Lutidine → 3-Cyano-3-(4-fluorophenyl)cyclobutan-1-yl t-butyldimethylsilyl ether
Reaction equation
[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH2:6][CH:5]([OH:7])[CH2:4]1)#[N:2].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])(=O)=O>ClCCl>[Si:29]([O:7][CH:5]1[CH2:6][C:3]([C:1]#[N:2])([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[CH2:4]1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]Participants
Procedure
3-cyano-3-(4-fluorophenyl)cyclobutan-1-ol (112, 19.8 g, 103.6 mmol) was dissolved in dichloromethane (200 mL) under argon, then 2,6-lutidine (27.78 g, 30.1 mL, 259 mmol) was added and the solution cooled to 0° C. tert-Butyldimethylsilyl trifluoromethanesulphonate (32.9 g, 28.6 mL, 124.3 mmol) was added dropwise and the stirred reaction mixture was then allowed to warm up to room temperature overnight. The reaction mixture was washed successively with water, hydrochloric acid (0.1M), saturated sodium bicarbonate solution and brine before being dried over sodium sulphate. Filtration and evaporation gave 32.9 g of a yellow oil which was used in the next step without further purification. Rt=1.30 min (Method 18). Detected mass: 306.3 (M+H+).
Workup
- additionwas added dropwise
- customthe stirred reaction mixture
- washThe reaction mixture was washed successively with water, hydrochloric acid (0.1M), saturated sodium bicarbonate solution and brine
- dry with materialbefore being dried over sodium sulphate
- filtrationFiltration and evaporation
Sources & evidence
- ORD record
- ord-d60bf11c6d9442af99ff125359900d74
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541449B2
Reaction notes
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