Sulfuric Acid → 4-Piperidinol, 4-(t-butyl)-1-((10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-, (+-)-

HRID 1449057ノート

反応式

HRID 1449057 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[C:12]([C:16]1([OH:39])[CH2:21][CH2:20][N:19]([C:22]([CH:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28][CH2:27][C:26]3[CH:35]=[CH:36][CH:37]=[CH:38][C:25]2=3)=O)[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13]>O1CCCC1>[C:12]([C:16]1([OH:39])[CH2:21][CH2:20][N:19]([CH2:22][CH:24]2[C:25]3[CH:38]=[CH:37][CH:36]=[CH:35][C:26]=3[CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=3)[CH2:18][CH2:17]1)([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 125156604-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-carbonyl]-4-piperidinolHCID 21226445Aluminium lithium hydride

生成物 1

HCID 30532464-Piperidinol, 4-(t-butyl)-1-((10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-, (+-)-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a cooled solution of lithium aluminum hydride in tetrahydrofuran (35.3 parts by volume of 0.9 M) is added 0.85 parts by volume of concentrated sulfuric acid dropwise over 5 minutes. The resultant mixture is stirred at 0° C. for about 1 hour and then solution of 3 parts of 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-carbonyl]-4-piperidinol in 50 parts by volume of tetrahydrofuran is added over a 5 minute period. The resultant mixture is allowed to warm to room temperature and stirred at that temperature for about 24 hours. Then, the mixture is cooled in an ice bath and quenched with the careful sequential addition of 1.2 part by volume of water, 1.2 part by volume of 15% sodium hydroxide, and 3.6 parts by volume of water. The resultant mixture is stirred for about 4 hours, the aluminum salts removed by filtration and washed well with ethyl ether. The filtrate is concentrated in vacuo to give 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)methyl]-4-piperidinol, as a colorless glass which crystallizes on standing. This compound is identical to that obtained in Example 1.

後処理

  1. temperatureThen, the mixture is cooled in an ice bath
  2. customquenched with the careful sequential addition of 1.2 part by volume of water, 1.2 part by volume of 15% sodium hydroxide, and 3.6 parts by volume of water
  3. stirringThe resultant mixture is stirred for about 4 hours
  4. customthe aluminum salts removed by filtration
  5. washwashed well with ethyl ether
  6. concentrationThe filtrate is concentrated in vacuo

出典と根拠

ORDレコード
ord-d35aceef99684f1bb6ebb3b34e1af130
出典データセット
uspto-grants-1980_02
特許番号
US04188485

反応ノート

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