2-Thiopheneacetyl chloride → (S)-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxylate

HRID 432814Notes

Reaction equation

HRID 432814 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1C=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:20]1C=CC=C1CC(Cl)=O>>[S:20]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:2][C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)=[O:8]

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Product 1

HCID 9838651(S)-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxylate

Procedure

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with commercially available S-ethyl nipecotate (1.0 g; 6.37 mmol; Chemi SpA; Italy) and 2-thiopheneacetyl chloride (785 μl; 6.37 mmol). The crude product was distilled as 225° C./0.1 torr, giving (S)-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxylate (1.23 g) as a light yellow oil. MS m/z (positive ion), 585 (dimer+Na+; 10), 304 (M+Na+; 50), 282 (MH+; 100), 158 (50). OR (MeOH; 589) +62.96°. Product was shown to be >98% ee by chiral capillary electrophoresis using a 20% solution of ·-HSCD (highly sulfated cyclodextrin) at a voltage of 20 kV.

Workup

  1. distillationThe crude product was distilled as 225° C./0.1 torr

Sources & evidence

ORD record
ord-d647a3e4e13448d48a64f6e64481b53f
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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