Ammonium formate → 1-(1-Methylethyl)-5-(1,1-dimethylethoxy)carbonyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole

HRID 1769089ノート

反応式

HRID 1769089 の反応式
C([O-])=O.[NH4+].[CH2:5]=[C:6]([C:8]1[S:9][CH:10]=[C:11]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][C:12]=12)[CH3:7]>CO.[Pd]>[CH3:7][CH:6]([C:8]1[S:9][CH:10]=[C:11]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13][C:12]=12)[CH3:5]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 189470701-(1-Propen-2-yl)-5-(1,1-dimethylethoxy)carbonyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole

生成物 1

HCID 189470581-(1-Methylethyl)-5-(1,1-dimethylethoxy)carbonyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole収率 63.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

3.7 g (59 mmol) of ammonium formate and then 0.9 g of 10% palladium-on-charcoal are added to a solution of 0.78 g (2.9 mmol) of 1-(1-propen-2-yl)-5-(1,1-dimethylethoxy)carbonyl-5,6-dihydro-4H-thieno[3, 4-c]pyrrole in 40 ml of methanol. The reaction mixture is heated at reflux for 8 hours, then filtered on a Celite column and evaporated to dryness. The residue is taken up in 50 ml of ethyl acetate, washed with 20 ml of water, dried over sodium sulphate and evaporated to dryness. After purification on a silica column using the 1/4 ethyl acetate/hexane eluent mixture, 0.49 g of an oily product is obtained. Yield 63%.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 8 hours
  3. filtrationfiltered on a Celite column
  4. customevaporated to dryness
  5. washwashed with 20 ml of water
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness
  8. customAfter purification on a silica column

出典と根拠

ORDレコード
ord-76aac0f306ea4225ba4758b22a048f86
出典データセット
uspto-grants-1995_01
特許番号
US05380742

反応ノート

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