Sodium Iodide → 5-acetyl-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

HRID 481081

反応式

HRID 481081 の反応式
[Bi](Cl)(Cl)Cl.[I-].[Na+].[C:7](Cl)(=[O:9])[CH3:8].[CH2:11]([O:13][C:14]([C:16]1[C:17]2[C:32]([O:33][Si](C)(C)C)=[CH:31][CH2:30][CH2:29][CH2:28][C:18]=2[N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:20]=1)=[O:15])[CH3:12]>C(Cl)Cl.CCOCC>[CH2:11]([O:13][C:14]([C:16]1[C:17]2[C:32](=[O:33])[CH:31]([C:7](=[O:9])[CH3:8])[CH2:30][CH2:29][CH2:28][C:18]=2[N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:20]=1)=[O:15])[CH3:12]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 24591Bismuth trichlorideHCID 207622254-trimethylsilanyloxy-7,8-dihydro-6H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

生成物 1

HCID 206056545-acetyl-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester収率 86%

試薬・触媒・溶媒 1

HCID 21881112Ethyl ether methylene chloride溶媒

実験手順

Bismuth (III) chloride (0.1 mmol) and sodium iodide (0.3 mmol) are transferred to a dried flask under nitrogen and 5 mL of a mixture of CH2Cl2/ether (9/1) is added by a syringe. This is followed by the addition of acetyl chloride (2.2 mmol) and the suspension is stirred for 5 min at RT. 4-trimethylsilanyloxy-7,8-dihydro-6H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (2 mmol) in 5 mL of the same solvent mixture is added. After 2 hours at RT, the mixture is quenched with 20 mL saturated NaHCO3 solution and extracted several times with CH2Cl2. The organic layers are combined, dried over Na2SO4 and evaporated in vacuo yielding 5-acetyl-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester as an oil (86%). LRMS 363.4 found (M+1) 364.2

後処理

  1. waitAfter 2 hours at RT
  2. customthe mixture is quenched with 20 mL saturated NaHCO3 solution
  3. extractionextracted several times with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-d3e8e5426a5845489a4b72e08857e8b7
出典データセット
uspto-grants-2003_11
特許番号
US06653471B2

関連ノート

読み込み中…