Pyridine → Benzyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 1751012노트

반응식

HRID 1751012 반응식
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>ClCCl>[O:17]=[C:10]1[C:11]2([CH2:12][CH2:13][N:14]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:15][CH2:16]2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one

생성물 1

HCID 58046755Benzyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate수율 79.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (10 g, 43.23 mmol, 1 equiv) in dichloromethane was treated with pyridine (6.99 ml, 86.46 mmol, 2 equiv) at 0° C. This was followed by the slow addition of benzyl chloroformate (6.39 ml, 45.4 mmol, 1.05 equiv). The reaction was stirred at ambient temperature for 16 h. The mixture was partitioned between dichloromethane and 10% citric acid followed by washes with water and brine. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford benzyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate as an off-white powder (12.5 g, 79%); MS for C21H23N3O3 m/z 366.18 (M+H)+.

후처리

  1. customThe mixture was partitioned between dichloromethane and 10% citric acid
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4b3fb4c73171418191b163d1a6465407
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156840B2

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