7-acetoxy-5-[1-(R)-phenylethyl]-5-azaspiro[2,4]heptane → 7-Acetoxy-5-azaspiro[2,4]heptane

HRID 1975340ノート

反応式

HRID 1975340 の反応式
[C:1]([O:4][CH:5]1[C:9]2([CH2:11][CH2:10]2)[CH2:8][N:7]([C@@H](C2C=CC=CC=2)C)[CH2:6]1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:4][CH:5]1[C:9]2([CH2:11][CH2:10]2)[CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 228504707-acetoxy-5-[1-(R)-phenylethyl]-5-azaspiro[2,4]heptaneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 224170847-Acetoxy-5-azaspiro[2,4]heptane収率 91.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A suspension of 1.5 g of compound 12 and 500 mg of lithium aluminum hydride in 30 ml of tetrahydrofuran was refluxed for 16 hours. 0.5 ml of water, 0.5 ml of 15% aqueous sodium hydroxide and 1.5 ml of water were added to the mixture in the mentioned order, and the mixture was stirred at room temperature for 30 minutes. The insoluble material was removed by filtration and the filtrate was concentrated to dryness to yield 1.4 g of 7-hydroxy-5-[1-(R)-phenylethyl]-5-azaspiro[2,4]heptane as a pale yellow oil. 5 ml of acetic anhydride and 5 ml of pyridine were added to 1.4 g of 7-hydroxy-5-[1-(R)-phenylethyl]-5-azaspiro[2,4]heptane which was cooled on an ice-bath. The mixture was stirred at room temperature for 3 hours. Ethyl acetate was added thereto and the solution was washed with saturated aqueous sodium bicarbonate and water, then, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to yield 1.6 g of 7-acetoxy-5-[1-(R)-phenylethyl]-5-azaspiro[2,4]heptane as a yellow oil. A mixture of 1.6 g of 7-acetoxy-5-[1-(R)-phenylethyl]-5-azaspiro[2,4]heptane and 1.2 g of palladium-on-carbon (50% water wet) in 20 ml of ethanol was shaken under 3.8 atm of pressured hydrogen atmosphere for 5 hours. During the reduction reaction, the reaction vessel was warmed by a tungsten lamp. The catalyst was removed by filtration and the solvent was removed under reduced pressure to give 880 mg of title compound 69 as an oil.

後処理

  1. customDuring the reduction reaction
  2. temperaturethe reaction vessel was warmed by a tungsten lamp
  3. customThe catalyst was removed by filtration
  4. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-ce9514a1038240788ae25c504955f6fe
出典データセット
uspto-grants-1994_02
特許番号
US05286723

反応ノート

読み込み中…