Hydrochloric Acid → 1-(4-Tert-butylphenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

HRID 1470934

反応式

HRID 1470934 の反応式
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[C:33]([C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1)([CH3:36])([CH3:35])[CH3:34].C(OCC)(=O)C.Cl>CN(C=O)C>[C:33]([C:37]1[CH:38]=[CH:39][C:40]([N:41]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH:6]2[C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[CH:42][CH:43]=1)([CH3:36])([CH3:34])[CH3:35]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 698614-Tert-ButylanilineHCID 596171791,4-Bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate

生成物 1

HCID 873789961-(4-Tert-butylphenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The product from Example 1C (3.67 g, 7.51 mmol) and 4-tert-butylaniline (11.86 ml, 75 mmol) in DMF (40 ml) was stirred under nitrogen at 50° C. for 4 h. The resulting mixture was diluted into ethyl acetate, treated with 1M HCl, stirred for 10 minutes and filtered to remove solids. The filtrate organic layer was washed twice with brine, dried with sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with ethyl acetate in hexane (5% to 30%) to give a solid. The solid was triturated in a minimal volume of 1:9 ethyl acetate/hexane to give a light yellow solid as a mixture of trans and cis isomers (1.21 g, 36%).

後処理

  1. filtrationfiltered
  2. customto remove solids
  3. washThe filtrate organic layer was washed twice with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate in hexane (5% to 30%)
  8. customto give a solid
  9. customThe solid was triturated in a minimal volume of 1:9 ethyl acetate/hexane
  10. customto give a light yellow solid
  11. additionas a mixture of trans and cis isomers (1.21 g, 36%)

出典と根拠

ORDレコード
ord-7898ff5637f64860afc0434a78d0f6cb
出典データセット
uspto-grants-2015_04
特許番号
US09006387B2

関連ノート

読み込み中…