Water → 8-benzyl-3-[(1R)-1-cyclopropylethoxy]-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

HRID 2188641노트

반응식

HRID 2188641 반응식
[CH:1]1([C@H:4]([OH:6])[CH3:5])[CH2:3][CH2:2]1.[H-].[Na+].[CH2:9]([N:16]1[CH2:22][C:21]2[N:23]=[CH:24][C:25](Cl)=[N:26][C:20]=2[O:19][CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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>[CH2:9]([N:16]1[CH2:22][C:21]2[N:23]=[CH:24][C:25]([O:6][C@@H:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:5])=[N:26][C:20]=2[O:19][CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6999829(1R)-1-cyclopropylethan-1-olHCID 866489818-Benzyl-3-chloro-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

생성물 1

HCID 669931558-benzyl-3-[(1R)-1-cyclopropylethoxy]-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine수율 67.2%

시약·촉매·용매 3

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

실험 절차

To a solution of (1R)-1-cyclopropylethanol (130 mg) in toluene (3 mL) was added sodium hydride (120 mg), and the mixture was stirred under a nitrogen atmosphere at room temperature for 15 min. A mixture of 8-benzyl-3-chloro-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (415 mg), BINAP (41 mg), Pd2(dba)3 (28 mg) and toluene (3 mL) was added, and the mixture was stirred under an argon atmosphere at 100° C. for 3 hr. Water was added to the reaction solution, and the resultant 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 basic silica gel column chromatography (solvent gradient; 5→50% ethyl acetate/hexane) to give the title compound (329 mg, 67%) as a yellow oil.

후처리

  1. additionwas added
  2. stirringthe mixture was stirred under an argon atmosphere at 100° C. for 3 hr
  3. extractionthe resultant 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 basic silica gel column chromatography (solvent gradient; 5→50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-d0fd7c17a73b43cbbab45a2554898073
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324201B2

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