Ethyl Acetate → Benzyl ethyl piperidine-1,3-dicarboxylate

HRID 659618Notes

Reaction equation

HRID 659618 reaction equation
C([O-])(O)=O.[Na+].[NH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7]1.[C:17](Cl)(=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOC(C)=O>O>[N:6]1([C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])[CH2:11][CH2:10][CH2:9][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 98969Ethyl nipecotateHCID 516892Sodium Bicarbonate

Product 1

HCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250-mL round-bottomed flask was charged with a solution of NaHCO3 (10.7 g, 127.38 mmol, 2.00 equiv) in H2O (80 mL), ethyl piperidine-3-carboxylate (10 g, 63.69 mmol, 1.00 equiv) and benzyl carbonochloridate (11.9 g, 70.00 mmol, 1.10 equiv). The resulting solution was stirred for 16 hours at room temperature. The progress was monitored by TLC (EtOAc: PE=1:5). Upon completion, the resulting solution was extracted with ethyl acetate (3×50 mL). Combined organic layers were dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:100) afford 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate as pale yellow oil (11.4 g, (62%).

Workup

  1. extractionUpon completion, the resulting solution was extracted with ethyl acetate (3×50 mL)
  2. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated on a rotary evaporator
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluted with ethyl acetate/petroleum ether (1:100)

Sources & evidence

ORD record
ord-8e2c050c0da94493b24b1653ec6ea4ec
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

Loading…