Benzaldehyde → (S)-ethyl 1-benzyl-3-piperidinecarboxylate

HRID 432830Notes

Reaction equation

HRID 432830 reaction equation
[NH:1]1[CH2:11][CH2:10][CH2:9][C@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([BH3-])#N.[Na+]>CO.ClCCl>[CH2:12]([N:1]1[CH2:11][CH2:10][CH2:9][C@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 187784Ethyl (3S)-piperidine-3-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 763479(S)-ethyl 1-benzyl-3-piperidinecarboxylateYield 39.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-ethyl nipecotate (309.1 mg; 1.97 mmol) was dissolved in anhydrous methanol (8 ml) and commercially available benzaldehyde (200 μl; 1.97 mmol) was added, followed by sodium cyanoborohydride (234 mg; 3.72 mmol). This mixture was allowed to stir at ambient temperature for 23 hours and was then diluted with dichloromethane. The dichloromethane was washed with water, then washed with saturated sodium chloride solution, dried with anhydrous potassium carbonate, and evaporated under reduced pressure at ambient temperature. The crude product was purified by chromatography on silica eluting with 50% ethyl acetate/50% hexane, giving (S)-ethyl 1-benzyl-3-piperidinecarboxylate (192.7 mg) as a colorless oil. MS mi/z (positive ion) 248 (MH+; 100).

Workup

  1. washThe dichloromethane was washed with water
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous potassium carbonate
  4. customevaporated under reduced pressure at ambient temperature
  5. customThe crude product was purified by chromatography on silica eluting with 50% ethyl acetate/50% hexane

Sources & evidence

ORD record
ord-472ed590b85742f8a3342adc795a622e
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

Loading…