Pyridine → Tert-butyl 6-{amino[({[(2-ethylhexyl)oxy]carbonyl}oxy)-imino]methyl}-4-{[tert-butyl(dimethyl)silyl]oxy}spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 420154ノート

反応式

HRID 420154 の反応式
[NH2:1][C:2](=[N:33][OH:34])[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[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].N1C=CC=CC=1.Cl[C:42]([O:44][CH2:45][CH:46]([CH2:51][CH3:52])[CH2:47][CH2:48][CH2:49][CH3:50])=[O:43]>CN(C=O)C>[NH2:1][C:2](=[N:33][O:34][C:42]([O:44][CH2:45][CH:46]([CH2:51][CH3:52])[CH2:47][CH2:48][CH2:49][CH3:50])=[O:43])[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[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 76650868Tert-butyl 6-[amino(hydroxyimino)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}spiro[chroman-2,4'-piperidine]-1'-carboxylate

生成物 1

HCID 76650869Tert-butyl 6-{amino[({[(2-ethylhexyl)oxy]carbonyl}oxy)-imino]methyl}-4-{[tert-butyl(dimethyl)silyl]oxy}spiro[chroman-2,4'-piperidine]-1'-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 6-[amino(hydroxyimino)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}spiro[chroman-2,4′-piperidine]-1′-carboxylate in 80 mL of DMF were added 3.78 mL of pyridine and 8.4 mL of 2-Ethylhexyl chloroformate at 0° C., and the reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was poured into ice-cold brine, and extracted with AcOEt twice. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in reduced pressure to give a crude product, which was used in the next step without further purification.

後処理

  1. additionThe reaction mixture was poured into ice-cold brine
  2. extractionextracted 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

出典と根拠

ORDレコード
ord-c5514936da184b3c9b9fe63e2ef8b893
出典データセット
uspto-grants-2012_01
特許番号
US08093389B2

反応ノート

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