ethyl 4-methylene-7,8-dihydro-4H-thieno[2,3-d]azepine-6(5H)-carboxylate → 4-Methyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

HRID 446716Notes

Reaction equation

HRID 446716 reaction equation
[CH2:1]=[C:2]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][C:4]2[S:14][CH:15]=[CH:16][C:3]1=2>C(O)C>[CH3:1][CH:2]1[C:3]2[CH:16]=[CH:15][S:14][C:4]=2[CH2:5][CH2:6][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8]1

Participants

3

Reactant 1

HCID 58293774ethyl 4-methylene-7,8-dihydro-4H-thieno[2,3-d]azepine-6(5H)-carboxylate

Product 1

HCID 593025564-Methyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1030 (310 mg, 1.31 mmol) was dissolved in ethanol (50 mL). The solution was degassed three times before addition of 10% Pd/C (100 mg). The flask was charged with hydrogen at atmospheric pressure (H2 balloon) and stirred at RT for 14 hours. The catalyst was removed by filtration through diatomaceous earth and the volatiles removed under reduced pressure to yield ethyl 4,5,7,8-tetrahydro-4-methylthieno[3,2-d]azepine-6-carboxylate (Compound 1031), which was used in subsequent reactions without further purification.

Workup

  1. customThe solution was degassed three times
  2. additionbefore addition of 10% Pd/C (100 mg)
  3. additionThe flask was charged with hydrogen at atmospheric pressure (H2 balloon)
  4. customThe catalyst was removed by filtration through diatomaceous earth
  5. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-90d4f64eb0954a16a562fc473a1adc14
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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