2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → Tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-((methylamino)carbonyl)piperidine-1-carboxylate

HRID 39678

反応式

HRID 39678 の反応式
[NH2:1][C:2]1([C:15]([NH:17][CH3:18])=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[O:19]1[C:24]2[CH:25]=[CH:26][C:27]([CH:29]=O)=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:19]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][NH:1][C:2]3([C:15]([NH:17][CH3:18])=[O:16])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:6][CH2:7]3)=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1

参加物

8

反応物 4

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58893187Tert-butyl 4-amino-4-(methylcarbamoyl)piperidine-1-carboxylate

生成物 1

HCID 67538791Tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-((methylamino)carbonyl)piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To 5 mL of a dichloromethane solution containing 0.30 g of tert-butyl 4-amino-4-((methylamino)carbonyl)piperidine-1-carboxylate, 0.16 g of 2,3-dihydro-1,4-benzodioxin-6-carbaldehyde and 57 μL of acetic acid were added, the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with 0.32 g of sodium triacetoxyborohydride and stirred at the same temperature for 30 minutes. Thereto were added chloroform and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to obtain 0.31 g of a pale yellow oily substance, tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-((methylamino)carbonyl)piperidine-1-carboxylate.

後処理

  1. additionwere added
  2. stirringstirred at the same temperature for 30 minutes
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washthe resultant solution was washed sequentially with water
  6. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

出典と根拠

ORDレコード
ord-e15549b6a8e941b89f1e8161579091a5
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

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