Lithium Hexamethyldisilazide → HCID 59511160, compound
Reaction equation
[C:1]([CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[P:27](OCl)([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28]>C1COCC1>[C:1]([CH:3]([P:27]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28])[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2]Participants
Procedure
In a 100 ml 3 necked round bottom flask, intermediate tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate (7 g) was taken in dry THF (125 ml) under nitrogen. lithium bis trimethylsilyl amide (10.8 g) was added dropwise at −78° C. and stirred for 1 hr, then diethyl chloro phosphate (5.84 g) in 5 ml dry THF was added drop wise to the above reaction mixture. Reaction mixture was stirred at −78° C. for 1 hour. TLC was checked no starting material and the reaction mixture was quenched with saturated ammonium chloride (250 ml) and ethyl acetate was added. The organic layer was washed with brine, dried and concentrated. The crude product was purified by column chromatography using 230-400 silica gel 2.5% methanol\chloroform as eluent to give compound tert-butyl 4-(cyano(diethoxyphosphoryl)methyl)piperazine-1-carboxylate as yellow liquid.
Workup
- customReaction mixture
- stirringwas stirred at −78° C. for 1 hour
- customthe reaction mixture was quenched with saturated ammonium chloride (250 ml) and ethyl acetate
- additionwas added
- washThe organic layer was washed with brine
- customdried
- concentrationconcentrated
- customThe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-d39b5e62d3f54eee8fd62bfc194bc72a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807671B2
Reaction notes
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