4-(2-Thienyl)Butyric Acid → HCID 54206822, compound

HRID 432823

Reaction equation

HRID 432823 reaction equation
[S:1]1[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)=[CH:2]1.S1C=C[CH:21]=[C:20]1CCCC(O)=O.Cl.CN(C)CCCN=C=NCC.N1CCC[C@H](C(OCC)=O)C1>>[S:1]1[CH:2]=[CH:21][CH:20]=[C:5]1[CH2:4][CH2:3][CH2:6][N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]1

Participants

5

Reactant 4

HCID 783864-(2-Thienyl)Butyric AcidHCID 187784Ethyl (3S)-piperidine-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12114708Ethyl 1-(3-thiophenecarbonyl)-3-piperidinecarboxylate

Product 1

HCID 54206822HCID 54206822, compound

Procedure

This reaction was run in the same manner as ethyl 1-(3-thiophenecarbonyl)-3-piperidinecarboxylate, starting with commercially available 4-(2-thienyl)butyric acid (280 μl; 1.93 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (367.7 mg; 1.92 mmol) and (S)-ethyl nipecotate (300 μl; 1.94 mmol). The crude product was purified by chromatography on silica eluting with 30% ethyl acetatel70% hexane to 40% ethyl acetate/60% hexane in a single step gradient, giving (S)-ethyl 1-(2-thienylpropyl)-3-piperidinecarboxylate (181.7 mg) as a colorless oil. MS m/z (positive ion) 411 (MH++Et3N; 40), 332 (M+Na+; 30), 310 (MH+; 100), 101 (Et3NH+; 30).

Workup

  1. customThe crude product was purified by chromatography on silica eluting with 30% ethyl acetatel70% hexane to 40% ethyl acetate/60% hexane in a single step gradient

Sources & evidence

ORD record
ord-283ea38535cd40d29998bfed421b0407
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Linked notes

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