1,4-Dioxane → Tert-butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

HRID 717883ノート

反応式

HRID 717883 の反応式
C(O/C=C\[C:6]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH:7]=1)C.I([O-])(=O)(=O)=O.[Na+].[O:36]1CCOC[CH2:37]1>O.[Os](=O)(=O)(=O)=O>[CH:37]([C:6]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]2)[CH:7]=1)=[O:36]

参加物

6

反応物 3

HCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 86706862tert-butyl 4-{[6-[(Z)-2-ethoxyvinyl]-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

生成物 1

HCID 86706863Tert-butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回

実験手順

tert-Butyl 4-{[6-[(Z)-2-ethoxyvinyl]-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate (0.80 g, 1.9 mmol, from Step 2) was dissolved in 1,4-dioxane (56 mL) and water (14 mL), then sodium periodate (1.2 g, 5.8 mmol) was added followed by osmium tetraoxide (4 wt % in water, 0.424 mL, 0.0666 mmol). After stirring for 24 hours, the reaction mixture was partitioned between water and EtOAc, the phases were separated and the aqueous phase was extracted with additional EtOAc. The combined organic extracts were washed with water, then sat'd NaCl, dried over Na2SO4, filtered and solvent removed in vacuo. The crude product was used in the next reaction without purification. LCMS (M+H)+: 375.0; (M+H2O+H)+: 393.0.

後処理

  1. customthe reaction mixture was partitioned between water and EtOAc
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with additional EtOAc
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customThe crude product was used in the next reaction without purification

出典と根拠

ORDレコード
ord-10d56eae0c6e44028d0e2ce66a2effa0
出典データセット
uspto-grants-2015_11
特許番号
US09193733B2

反応ノート

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