Ammonium Chloride → Methyl (1aRS,7bSR)-5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927931노트

반응식

HRID 927931 반응식
Br[C:2]1(Br)[CH:12]2[CH:3]1[CH2:4][O:5][C:6]1[C:11]2=[CH:10][CH:9]=[C:8]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]=1[C:20]([O:22][CH3:23])=[O:21].[Cl-].[NH4+]>C(O)C.[Zn]>[CH3:16][C:15]([CH3:18])([CH3:17])[C:14]([NH:13][C:8]1[C:7]([C:20]([O:22][CH3:23])=[O:21])=[C:6]2[C:11]([CH:12]3[CH2:2][CH:3]3[CH2:4][O:5]2)=[CH:10][CH:9]=1)=[O:19]

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 86713294Methyl 1,1-dibromo-5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2회

생성물 1

HCID 77979731Methyl (1aRS,7bSR)-5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate수율 41.7%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 702Ethanol용매

실험 절차

Methyl (1aRS,7bSR)-1,1-dibromo-5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (Intermediate 44, 1.13 g) was suspended in ethanol (30 mL). Zinc dust (1.17 g), followed by ammonium chloride (1.31 g) were added and the reaction mixture was heated to reflux, under an atmosphere of nitrogen, for 6 hours. After cooling, the solid was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ether and cyclohexane, with a gradient of 5-12.5% to give methyl (1aRS,7bSR)-5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.310 g) as a colourless oil.

후처리

  1. additionwere added
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux, under an atmosphere of nitrogen, for 6 hours
  4. temperatureAfter cooling
  5. filtrationthe solid was filtered off
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ether and cyclohexane, with a gradient of 5-12.5%

출처 및 근거

ORD 기록
ord-c09cffa2ccfd4e1cb053a540822dadc3
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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