2-Phenylpropionic acid → Ethyl 1-(2-phenylpropanoyl)-3-piperidinecarboxylate

HRID 432825

Reaction equation

HRID 432825 reaction equation
S1[CH:5]=[CH:4][C:3]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]2)=[O:7])=[CH:2]1.[C:19]1(C(C)C(O)=O)[CH:24]=CC=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC.N1CCC[C@H](C(OCC)=O)C1>>[C:4]1([CH:3]([CH3:2])[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]2)=[O:7])[CH:21]=[CH:20][CH:19]=[CH:24][CH:5]=1

Participants

5

Reactant 4

HCID 102962-Phenylpropionic acidHCID 187784Ethyl (3S)-piperidine-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12114708Ethyl 1-(3-thiophenecarbonyl)-3-piperidinecarboxylate

Product 1

HCID 53689184Ethyl 1-(2-phenylpropanoyl)-3-piperidinecarboxylate

Procedure

This reaction was run in the same manner as ethyl 1-(3-thiophenecarbonyl)-3-piperidinecarboxylate, starting with commercially available 2-phenylpropionic acid (265 μl; 1.94 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (371.3 mg; 1.94 mmol) and (S)-ethyl nipecotate (300 μl; 1.94 mmol). Crude product was purified by chromatography on silica eluting with 25% ethyl acetate/75% hexane, giving (S)±ethyl 1-(2-phenylpropionyl)-3-piperidinecarboxylate (268.9 mg) as a colorless oil. MS m/z (positive ion) 290 (MH+; 100), 142 (55), 115 (50).

Workup

  1. customCrude product was purified by chromatography on silica eluting with 25% ethyl acetate/75% hexane

Sources & evidence

ORD record
ord-b0568fc3ff6648e6b1d62d8085f6f4e5
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Linked notes

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