Formaldehyde → tert-butyl 4,5-Dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate

HRID 2093100Notes

Reaction equation

HRID 2093100 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C=O.[CH3:18]C1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[S:12]1[C:11]2[CH2:18][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15])[CH2:8][CH2:9][C:10]=2[CH:14]=[CH:13]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 19600076(2-Thiophen-3-YL-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 17389936tert-butyl 4,5-Dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl[2-(3-thienyl)ethyl]carbamate in toluene was added paraformaldehyde (2 equi.) and catalytic amount of PTSA and reaction mixture was then refluxed in dean stark apparatus for 4 hrs. Reaction mass wan then concentrated and extracted with dichloromethane dried over sodium sulphate and evaporated to yield tert-butyl 4,7-dihydrothieno[2,3-c]pyridine-6(5H)— carboxylate.

Workup

  1. temperaturewas then refluxed in dean stark apparatus for 4 hrs
  2. customReaction mass
  3. concentrationwan then concentrated
  4. extractionextracted with dichloromethane
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-b043a35771784d9eb6582b7dc61ab5b2
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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