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

HRID 927931ノート

反応式

HRID 927931 の反応式
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]

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 86713294Methyl 1,1-dibromo-5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-c09cffa2ccfd4e1cb053a540822dadc3
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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