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

HRID 1860282노트

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HRID 1860282 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 702Ethanol용매

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온도
60 °C

실험 절차

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, a, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ea9cf3097a947858ca0b1564b81990e
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528534B2

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