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

HRID 1690613Notes

Reaction equation

HRID 1690613 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-193e99effc42430ba6ebf51bbeb5bd79
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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