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

HRID 420604
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HRID 420604 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-ddefaf1682da452d843f956865393ee4
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08097610B2

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