Hydrochloric Acid → 4-oxo-5,6,7,8-tetrahydro-1H-cyclohepta[b]pyrrole-3-carboxylic acid

HRID 906

反応式

HRID 906 の反応式
[O:1]=[C:2]1[C:11]2[C:10]([C:12]([O:14]CC)=[O:13])=[CH:9][NH:8][C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl>[OH-].[Na+].C(O)C>[O:1]=[C:2]1[C:11]2[C:10]([C:12]([OH:14])=[O:13])=[CH:9][NH:8][C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 18696565Ethyl 4-oxo-1,4,5,6,7,8-hexahydrocyclohepta[B]pyrrole-3-carboxylate

生成物 1

HCID 223187424-oxo-5,6,7,8-tetrahydro-1H-cyclohepta[b]pyrrole-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A mixture of ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate (3.48 g, 15.7 mmol) and ammonium acetate (2.41 g, 31.3 mmol) in N,N-dimethylformamide (25 mL) was heated at 115° C. for 6 hours. The mixture was concentrated in vacuo, ice water was added, then extracted 2× with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate then brine, dried over sodium sulfate, filtered through a small pad of Silica gel (1:19 methyl alcohol/dichloromethane), and the filtrate concentrated in vacuo to give ethyl 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylate (1.76 g). A solution of this ester in aqueous 5N sodium hydroxide (30 mL) and ethyl alcohol (6 mL) was heated at reflux for 1 hour, then cooled in an ice bath. The mixture was acidified with hydrochloric acid, and the precipitate collected, rinsed with water followed by diethyl ether and allowed to dry to give 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid (1.17 g). m.p. 225°-227° C.

後処理

  1. temperatureat reflux for 1 hour
  2. temperaturecooled in an ice bath
  3. customthe precipitate collected
  4. washrinsed with water
  5. customto dry

出典と根拠

ORDレコード
ord-2b79dceda53e44969acdb4dd9345d9f9
出典データセット
uspto-grants-1998_03
特許番号
US05723462

関連ノート

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