Acetic Acid → 1-(2,2-Diphenylethyl)-3-carboxy piperidine

HRID 365450Notes

Reaction equation

HRID 365450 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1.[C:10]1([CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([BH3-])#N.[Na+].CC(O)=O>CO>[C:10]1([CH:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:17][N:1]2[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4498Nipecotic AcidHCID 13696DiphenylacetaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 232911301-(2,2-Diphenylethyl)-3-carboxy piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nipecotic acid (300 mg, 2.38 mmol), diphenylacetaldehyde (1.26 mL, 7.13 mmol), sodium cyanoborohydride (448 mg, 7.13 mmol), and HOAc (204 uL, 3.57 mmol) were dissolved in MeOH (20 mL) and stirred at ambient temperature overnight. The solution was concentrated under reduced pressure, take up in ether and 1N NaOH, extract with ether (3×), acidify the aqueous layer with 1N HCl, and extract with EtOAc (3×). The EtOAc layers were dried (MgSO4) and concentrated to give the title compound without further purification.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. extraction1N NaOH, extract with ether (3×)
  3. extractionextract with EtOAc (3×)
  4. dry with materialThe EtOAc layers were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a8b2c8b69a274b6493c2d0395829d20a
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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