Triethylamine → trans-3-hydroxy-4-[(1H-imidazol-5-yl)carbonylamino]-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide

HRID 981311ノート

反応式

HRID 981311 の反応式
C(N(CC)CC)C.[CH:8]1[N:9]=[CH:10][N:11]2[C:16]=1[C:15](=[O:17])[N:14]1C=N[CH:20]=[C:13]1[C:12]2=[O:21].N[C@@H]1C[CH2:27][N:26]([CH:29]([CH3:49])[CH2:30][C:31]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH2:25][C@H]1O>CN(C)C=O>[OH:21][C@H:12]1[C@H:13]([NH:14][C:15]([C:16]2[NH:11][CH:10]=[N:9][CH:8]=2)=[O:17])[CH2:20][CH2:27][N:26]([CH:29]([CH3:49])[CH2:30][C:31]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:32]([N:34]([CH3:35])[CH3:36])=[O:33])[CH2:25]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1051510Diimidazo[1,5-a:1',5'-d]pyrazine-5,10-dioneHCID 67928771trans-4-amino-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide

生成物 1

HCID 86744578trans-3-hydroxy-4-[(1H-imidazol-5-yl)carbonylamino]-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide収率 23%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

2.8 Parts of N,N-diethylethanamine were added to a solution of 1 part of 5H, 10H-diimidazo[1,5-a:1',5'-d]pyrazine-5,10-dione in 36 parts of N,N-dimethylformamide. The thus obtained suspension was added dropwise to a stirred and heated (70° C.) solution of 3.95 parts of trans-4-amino-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide in 18 parts of N,N-dimethylformamide. Upon complete addition, stirring was continued overnight at 70° C. After evaporation, the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was further purified by column chromatography (HPLC) over silica gel using a mixture of trichloromethane, methanol and methanol, saturated with ammonia, (90:9:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was pulverised and evaporated again, yielding 1.13 parts (23%) of trans-3-hydroxy-4-[(1H-imidazol-5-yl)carbonylamino] -N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 155.0° C. (compound 43).

後処理

  1. additionThe thus obtained suspension was added dropwise to
  2. additionUpon complete addition
  3. stirringstirring
  4. customAfter evaporation
  5. customthe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was further purified by column chromatography (HPLC) over silica gel using
  10. additiona mixture of trichloromethane, methanol and methanol
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customevaporated again

出典と根拠

ORDレコード
ord-b6a491be0934422c9fd8e464ed95824e
出典データセット
uspto-grants-1991_02
特許番号
US04990521

反応ノート

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