Hydrochloric Acid → 1-(3-(2-(1-Benzothiophene-6-yl)ethoxy)propyl)-3-azetidinol

HRID 7438

反応式

HRID 7438 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[CH:12]=[CH:13][S:14][C:10]=2[CH:9]=1.Cl.[NH:18]1[CH2:21][CH:20]([OH:22])[CH2:19]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.C(OCC)(=O)C.O>[S:14]1[C:10]2[CH:9]=[C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:18]3[CH2:21][CH:20]([OH:22])[CH2:19]3)[CH:16]=[CH:15][C:11]=2[CH:12]=[CH:13]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 219900846-(2-(3-Chloropropoxy)ethyl)-1-benzothiophene

生成物 1

HCID 235455641-(3-(2-(1-Benzothiophene-6-yl)ethoxy)propyl)-3-azetidinol収率 24.5%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

In 5 mL of dimethyl sulfoxide was dissolved 1.00 g of 6-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and 0.86 g of 3-azetidinol hydrochloride and 1.63 g of potassium carbonate were added to the solution. The resulting mixture was stirred at 75° C. for 2.5 hours and then at 95° C. for 1.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 6 mol/L hydrochloric acid, and the aqueous layer was separated. Ethyl acetate was added to the aqueous layer and the. pH was adjusted to 10 with a 2 mol/L aqueous sodium hydroxide solution, after which the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 5:1) to obtain 0.28 g of 1-{3-[2-(1-benzothiophen-6-yl)ethoxy]propyl}-3-azetidinol as a colorless oil.

後処理

  1. additionwere added to the solution
  2. waitat 95° C. for 1.5 hours
  3. temperatureAfter the reaction mixture was cooled
  4. customthe aqueous layer was separated
  5. additionEthyl acetate was added to the aqueous layer
  6. customafter which the organic layer was separated
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 5:1)

出典と根拠

ORDレコード
ord-5c37f61942b04b9e986f75c9bbc72dab
出典データセット
uspto-grants-2006_08
特許番号
US07087594B2

関連ノート

読み込み中…