Potassium Hydroxide → 5-(4-Fluorobenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

HRID 1262954ノート

反応式

HRID 1262954 の反応式
[F:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][C:15](C(OC)=O)([C:16]([O:18]C)=[O:17])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.FC1C=CC(C(C2N3CCC(C(OC)=O)C3=CC=2)=O)=CC=1.[OH-].[K+]>CO.O>[F:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH:15]([C:16]([OH:18])=[O:17])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 12915912dimethyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylateHCID 12915913methyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

生成物 1

HCID 129159145-(4-Fluorobenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid収率 80%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of the mixture of dimethyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylate and methyl 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate (0.200 g) in methanol (5 ml) and water (3 ml) containing potassium hydroxide (0.5 g) was heated at reflux temperature for 1 hour. The solvent was removed in vacuo, water was added to the residue and the solution waas made acidic with 10% hydrochloric acid solution. The product was extracted into ethyl acetate, the extract was dried and evaporated. The solid residue on crystallization from ethyl acetate-hexane gave 5-(4-fluorobenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid (0.124 g, 80%) m.p. 163°. A mixed m.p. with an authentic specimen (m.p. 170°) had m.p. 165°. The IR spectrum was identical to that of the authentic sample.

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour
  3. customThe solvent was removed in vacuo, water
  4. additionwas added to the residue
  5. extractionThe product was extracted into ethyl acetate
  6. customthe extract was dried
  7. customevaporated
  8. customThe solid residue on crystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-08937b81d2ce45709e00fafe1f54de8b
出典データセット
uspto-grants-1984_06
特許番号
US04454326

反応ノート

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