Hydrochloric Acid → 5,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(piperidine-1-carbonyl)-5H-furan-2-one

HRID 1602534ノート

反応式

HRID 1602534 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.C([O:13][C:14]([C:16]1[C:17](=[O:33])[O:18][C:19]([CH3:32])([CH3:31])[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)=O)C.Cl>C(Cl)Cl>[CH3:31][C:19]1([CH3:32])[O:18][C:17](=[O:33])[C:16]([C:14]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:13])=[C:20]1[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 16682925TrimethylaluminumHCID 544790785,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-2-oxo-2,5-dihydrofuran-3-carboxylic acid ethyl ester

生成物 1

HCID 219484885,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(piperidine-1-carbonyl)-5H-furan-2-one収率 50.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a room temperature solution of piperidine (284 mg, 3.33 mmol) in CH2Cl2 (5 mL) was added trimethylaluminum (2M in hexane, 1.7 mL, 3.4 mmol). After 15 min, the product from Step 1 (310 mg, 0.92 mmol) was added in one portion and the mixture was heated to reflux for 20h. The resulting solution was cooled and poured into 1M HCl (gas evolution). The organic layer was washed with brine, filtered through cotton and evaporated. Purification by flash chromatography (80% EtOAc/Hex) provided 175 mg of the title compound.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20h
  3. temperatureThe resulting solution was cooled
  4. washThe organic layer was washed with brine
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customPurification by flash chromatography (80% EtOAc/Hex)

出典と根拠

ORDレコード
ord-506188c1dfb142d2ae8200b6510e919d
出典データセット
uspto-grants-1999_11
特許番号
US05981576

反応ノート

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