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

HRID 1449057노트

반응식

HRID 1449057 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d35aceef99684f1bb6ebb3b34e1af130
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04188485

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