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

HRID 420604
ノート
印刷プレビュー

反応式

HRID 420604 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-ddefaf1682da452d843f956865393ee4
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097610B2

反応ノート

読み込み中…

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