Imidazole → tert-Butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-6-cyano-spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 1096922ノート

反応式

HRID 1096922 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][CH:6]2[OH:25])#[N:2].N1C=CN=C1.[CH3:31][C:32]([Si:35](Cl)([CH3:37])[CH3:36])([CH3:34])[CH3:33]>CN(C=O)C>[Si:35]([O:25][CH:6]1[C:5]2[C:22](=[CH:23][CH:24]=[C:3]([C:1]#[N:2])[CH:4]=2)[O:21][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:7]1)([C:32]([CH3:34])([CH3:33])[CH3:31])([CH3:37])[CH3:36]

参加物

5

反応物 3

HCID 795Imidazole2 回HCID 28928tert-Butyldimethylsilyl chloride2 回HCID 66649142tert-Butyl 6-cyano-4-hydroxy-spiro[chroman-2,4'-piperidine]-1'-carboxylate

生成物 1

HCID 66649537tert-Butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-6-cyano-spiro[chroman-2,4'-piperidine]-1'-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 15.1 g of tert-butyl 6-cyano-4-hydroxy-spiro[chroman-2,4′-piperidine]-1′-carboxylate in DMF were added 3.6 g of imidazole and 7.95 g of TBSCl at rt, and the reaction mixture was stirred at rt for 1d. To this reaction mixture was added 598 mg of imidazole and 1.3 g of TBSCl at rt, and the reaction mixture was stirred at rt for 1d. The reaction mixture was poured into ice-cold brine, and the aqueous mixture was extracted with AcOEt twice. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of hexane and AcOEt (100/0-80/20) as eluent to give the intended compound.

後処理

  1. additionThe reaction mixture was poured into ice-cold brine
  2. extractionthe aqueous mixture was extracted with AcOEt twice
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of hexane and AcOEt (100/0-80/20) as eluent
  9. customto give the intended compound

出典と根拠

ORDレコード
ord-6a6b934481a148a689f900a3a66777d5
出典データセット
uspto-grants-2012_03
特許番号
US08138197B2

反応ノート

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