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Triacetoxyperiodinane → 3-(2-Acetyl-8-fluoro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-3-yl)propanal

HRID 1867268
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HRID 1867268 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]3[C:11]([CH2:23][CH2:24][CH2:25][OH:26])([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]([C:14](=[O:16])[CH3:15])=[N:13][N:7]3[C:6]=2[CH:27]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:14]([C:12]1[C:11]([CH2:23][CH2:24][CH:25]=[O:26])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:8]2[CH2:9][O:10][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:27][C:6]=3[N:7]2[N:13]=1)(=[O:16])[CH3:15]
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참가 물질

5

반응물 3

HCID 159087TriacetoxyperiodinaneHCID 22607107sodium thiosulfate NaHCO3HCID 684487931-[8-fluoro-3-(3-hydroxypropyl)-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-2-yl]ethanone

생성물 1

HCID 766948773-(2-Acetyl-8-fluoro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-3-yl)propanal

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

1-[8-Fluoro-3-(3-hydroxypropyl)-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-2-yl]ethanone (5-8; a racemic mixture, 1.23 g, 3.34 mmol) was dissolved in anhydrous CH2Cl2 (20 mL) and was treated with Dess-Martin periodinane (2.26 g, 5.3 mmol) and the resulting cloudy yellow solution was stirred 1.5 h. Upon completion, the cloudy solution was treated with 10 mL sat. sodium thiosulfate/NaHCO3 solution (1:1) and stirred 30 min. The mixture was extracted with EtOAc (3×20 mL), and the combined organics were dried (MgSO4), filtered and concentrated. The crude residue 3-(2-acetyl-8-fluoro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-3-yl)propanal (5-9; a racemic mixture) was carried directly into the next transformation: MS (M+H+, C21H19FN2O3) 367.3 found 367.4 required.

후처리

  1. stirringstirred 30 min
  2. extractionThe mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialthe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-636799e827a44f85bab9798d15d266b1
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07632833B2

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