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

HRID 1690613ノート

反応式

HRID 1690613 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-193e99effc42430ba6ebf51bbeb5bd79
出典データセット
uspto-grants-2012_04
特許番号
US08153647B2

反応ノート

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