Acetic Acid → Ethyl 3-[2-(3-methoxypropoxy)-4'-(piperidin-1-ylmethyl)biphenyl-4-yl]propanoate

HRID 1690613노트

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HRID 1690613 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11](CCC(OCC)=O)[C:10]=2[O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:5][CH:4]=1)=O.[C:28]([OH:31])(=[O:30])[CH3:29].[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:39].[Na+].[C:52](=O)(O)[O-].[Na+]>ClC(Cl)C>[CH3:27][O:26][CH2:25][CH2:24][CH2:23][O:22][C:10]1[CH:11]=[C:12]([CH2:52][CH2:29][C:28]([O:31][CH2:38][CH3:39])=[O:30])[CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:1][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:4][CH:5]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86633299Ethyl 3-[4'-formyl-2-(3-methoxypropoxy)biphenyl yl]propanoate

생성물 1

HCID 66906385Ethyl 3-[2-(3-methoxypropoxy)-4'-(piperidin-1-ylmethyl)biphenyl-4-yl]propanoate수율 80%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

Ethyl 3-[4′-formyl-2-(3-methoxypropoxy)biphenyl yl]propanoate (1 g, 2.7 mmol) was dissolved in dichloroethane (20 mL). At 0° C., acetic acid (0.02 mL, 0.4 mmol) was added, followed by piperidine (0.25 g, 3 mmol) and sodium triacetoxyborohydride (0.86 g, 4 mmol) portionwise. The mixture was stirred at room temperature overnight. At, 0° C., saturated aqueous sodium bicarbonate solution was added. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were washed with brine and water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 0.95 g (80%) of the desired product as a brown oil.

후처리

  1. extractionThe aqueous layer was extracted three times with dichloromethane
  2. washThe combined organic layers were washed with brine and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-193e99effc42430ba6ebf51bbeb5bd79
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153647B2

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