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

HRID 2191256

반응식

HRID 2191256 반응식
[CH3:1][CH:2]([CH3:6])[CH:3]([OH:5])[CH3:4].[H-].[Na+].Cl[C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:17][O:18][C:19]=2[N:20]=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>[CH3:4][CH:3]([O:5][C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:17][O:18][C:19]=2[N:20]=1)[CH:2]([CH3:6])[CH3:1]

참가 물질

8

반응물 4

HCID 962WaterHCID 117323-Methyl-2-butanolHCID 24758Sodium hydrideHCID 57356939Tert-butyl 8-chloro-2,3-dihydropyrido[3,2-F][1,4]oxazepine-4(5H)-carboxylate

생성물 1

HCID 68427435tert-butyl 8-(1,2-dimethylpropoxy)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate수율 61%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매2회

반응 조건

온도
70 °C

실험 절차

To a solution of 3-methylbutan-2-ol (0.19 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-(1,2-dimethylpropoxy)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.36 g, 61%) as a yellow oil.

후처리

  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)

출처 및 근거

ORD 기록
ord-61143a012b0446e091c9f1c0d5be59d1
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329687B2

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