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Ammonium formate → HCID 57753401, 화합물

HRID 1930878
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HRID 1930878 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3[CH2:18][CH2:19][O:20][CH2:21][CH:22]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 577532705-(3,6-Dihydro-2H-pyran-4-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

생성물 1

HCID 57753401HCID 57753401, 화합물수율 92%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a stirred solution 7.27 mmol 5-(3,6-dihydro-2H-pyran-4-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester in 60 ml methanol were added 1.60 g 10% palladium on charcoal and 72.7 mmol ammonium formate and the mixture was heated at reflux for 30 min. The reaction mixture was then cooled to room temperature, filtered, and the filtrate concentrated in vacuo. The residue was taken up in THF and washed with brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (92% yield). MS (m/e): 248.3 ([M+H-Me2C═CH2]+, 100%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 min
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. washwashed with brine
  6. dry with materialThe organic phase was then dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-3f3ccc89639042a78ce975addaf23377
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08188139B2

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