Lithium Hexamethyldisilazide → 4-[2-(t-Butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile

HRID 420604Notes

Reaction equation

HRID 420604 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][CH:13]([C:16]#[N:17])[CH2:12][CH2:11]3)[S:9][C:5]=2[CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:33][CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37]>O1CCCC1.[Cl-].[Na+].O>[Si:36]([O:35][CH2:34][CH2:33][C:13]1([C:16]#[N:17])[CH2:14][CH2:15][N:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:19]=[CH:18][C:6]=3[N:7]=2)[CH2:11][CH2:12]1)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 579666861-(6-(Trifluoromethyl)benzo[d]thiazol-2-yl)piperidine-4-carbonitrile

Product 1

HCID 579664524-[2-(t-Butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile (1.00 g) in tetrahydrofuran (10 mL) was added lithium bis(trimethylsilyl)amide (3.21 mL) at −15° C. To the reaction solution was added (2-bromoethoxy)-t-butyldimethyl silane (689 μL). The mixture was stirred at 0° C. for 3 hours. To the reaction solution was added brine and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the obtained residue was purified by column chromatograph on silica gel to give the title compound (1.23 g). Yield: 82%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-ddefaf1682da452d843f956865393ee4
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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