Hydantoin → 1,3,8-Triazaspiro[4.5]decane-2,4-dione

HRID 1596684ノート

反応式

HRID 1596684 の反応式
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:12][CH2:11][N:10](C(OCC3C=CC=CC=3)=O)[CH2:9][CH2:8]2)[NH:3]1.C(OC(N1CCCCC1=O)=O)C1C=CC=CC=1.[H][H].N1CC(=O)NC1=O>C(O)C.[Pd].C(O)(=O)C>[NH:3]1[C:4]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5](=[O:7])[NH:6][C:2]1=[O:1]

参加物

8

反応物 4

HCID 10006HydantoinHCID 10425057Benzyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylateHCID 11096497Benzyl 2-oxopiperidine-1-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 1209891,3,8-Triazaspiro[4.5]decane-2,4-dione

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 14.6 g (48.1 mmol) benzyl 2,4-dioxo-1,3,8-triaza-spiro[4.5]decan-8-carboxylate (prepared from N-(benzyloxycarbonyl)piperidone by the method from J. Med. Chem. 1995, 38, 3772) in 250 ml dry ethanol were added 500 mg 10% Pd/C, and the mixture was filled into an autoclave. After stirring at 60° C. and 10 atm of hydrogen for 3 h no starting hydantoin could be detected by TLC. A precipitate had been formed which was redissolved by addition of 100 ml acetic acid. The catalyst was removed by filtration and the solution was concentrated in vacuo. Aqueous sodium bicarbonate solution was added until the mixture became a clear solution, and the title compound precipitated in two crops upon concentration in vacuo.

後処理

  1. additionthe mixture was filled into an autoclave
  2. customA precipitate had been formed which
  3. customThe catalyst was removed by filtration
  4. concentrationthe solution was concentrated in vacuo
  5. additionAqueous sodium bicarbonate solution was added until the mixture
  6. customthe title compound precipitated in two crops upon concentration in vacuo

出典と根拠

ORDレコード
ord-d30ed5b8172d439fbedb75f94161efd9
出典データセット
uspto-grants-2001_09
特許番号
US06291469B1

反応ノート

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