Water → tert-butyl 8-isobutoxy-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

HRID 2191251ノート

反応式

HRID 2191251 の反応式
[CH2:1]([OH:5])[CH:2]([CH3:4])[CH3:3].[H-].[Na+].Cl[C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:16][O:17][C:18]=2[N:19]=1.O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:5][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:16][O:17][C:18]=2[N:19]=1)[CH:2]([CH3:4])[CH3:3]

参加物

8

反応物 4

HCID 962WaterHCID 6560IsobutanolHCID 24758Sodium hydrideHCID 57356939Tert-butyl 8-chloro-2,3-dihydropyrido[3,2-F][1,4]oxazepine-4(5H)-carboxylate

生成物 1

HCID 68428582tert-butyl 8-isobutoxy-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate収率 58%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒2 回

反応条件

温度
70 °C

実験手順

To a solution of isobutyl alcohol (0.16 mL) in toluene (4 mL) was added sodium hydride (0.14 g), and the resulting mixture was stirred at 70° C. for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.50 g), BINAP (0.033 g), Pd2(dba)3 (0.024 g) and toluene (4 mL) was added, and the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give tert-butyl 8-isobutoxy-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.33 g, 58%) as a yellow oil.

後処理

  1. additionwas added
  2. stirringthe resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere
  3. extractionthe resulting product was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-020d6e24b5fd47b99e7247fa5492b884
出典データセット
uspto-grants-2012_12
特許番号
US08329687B2

反応ノート

読み込み中…