Acetone → Ethyl 1-isopropylpiperidine-4-carboxylate

HRID 1057738Notes

Reaction equation

HRID 1057738 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[CH3:12][C:13]([CH3:15])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH3:12][CH:13]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)[CH3:15]

Participants

6

Reactant 4

HCID 180AcetoneHCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 19900430Ethyl 1-isopropylpiperidine-4-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Ethyl isonipecotate (3.2 g, 20 mmol, 1 eq) was combined with acetone (5.8 g, 100 mmol, 5 eq), sodium triacetoxyborohydride (10.5 g, 50 mmol, 2.5 eq) and 1,2-dichloroethane (200 mL). The reaction mixture was stirred at rt for 72 h. Saturated aqueous NaHCO3 was added, and the mixture was extracted with CH2Cl2. The organic extracts were dried, filtered through a silica gel pad, and concentrated in vacuo to provide 3.72 g (93%) of ethyl 1-(1-methylethyl)-4-piperidine carboxylate as a colorless liquid.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. customThe organic extracts were dried
  3. filtrationfiltered through a silica gel pad
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d2185d5943d427bb76bd84db89ac2f7
Source dataset
uspto-grants-2003_02
Patent number
US06515004B1

Reaction notes

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