Dimethylformamide → 5-tert-Butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate

HRID 1158853Notes

Reaction equation

HRID 1158853 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl.[CH3:19]N(C=O)C.[SH:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CCN(CC)CC>[S:24]1[C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]=2[CH:19]=[C:25]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 12185Ethyl ThioglycolateHCID 24813Phosphorus oxychlorideHCID 7010304N-(tert-butoxycarbonyl)piperidine

Product 1

HCID 118454155-tert-Butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5-tert-butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate was prepared according to the procedure as outlined in Example 1, (Step 1). Starting from tert-butyl-1-piperidinecarboxylate (9.9 g, 50 mmol), POCl3 (6.3 g, 40 mmol) and DMF (3.8 g, 50 mmol). The chloroformyl intermediate was reacted with ethyl mercaptoacetate (6.0 g, 50 mmol) and Et3N. The product was purified by SiO2 column chromatography by eluting it with 3:1 hexane; ethylacetate. Yield: 8.7 g, 56%; White liquid. (M+H) 312.

Workup

  1. customThe product was purified by SiO2 column chromatography
  2. washby eluting it with 3:1 hexane

Sources & evidence

ORD record
ord-7d179052aaef45d29607dae1ad9a7a7b
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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