1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → tert-butyl 8-(m-fluorophenyl)-4,5-dihydro-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylate

HRID 477915Notes

Reaction equation

HRID 477915 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[O:15]=[C:16]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[CH:24][C:23](C(O)=O)=[C:22]2[N:17]1[CH2:18][CH2:19][C:20]1[CH:38]=[CH:37][S:36][C:21]=12>C1(C)C=CC=CC=1>[F:32][C:28]1[CH:27]=[C:26]([C:25]2[C:16](=[O:15])[N:17]3[C:22](=[C:23]([C:6]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5])[CH:24]=2)[C:21]2[S:36][CH:37]=[CH:38][C:20]=2[CH2:19][CH2:18]3)[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 19020416HCID 19020416, compound

Product 1

HCID 19020443tert-butyl 8-(m-fluorophenyl)-4,5-dihydro-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.96 ml of N,N-dimethylformamide di-t-butyl acetal was added dropwise within 20 minutes to a boiling solution of 0.34 g of 4,5-dihydro-7-oxo-8-(m-fluorophenyl)-7H-thieno[2,3-a]quinolizine-10-carboxylic acid in 5 ml of toluene. The mixture was heated under reflux for an additional 30 minutes, left to stand at room temperature overnight and then washed once with water, twice with saturated aqueous sodium bicarbonate solution and once with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate and there was obtained tert-butyl 8-(m-fluorophenyl)-4,5-dihydro-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylate of m.p. 135°-137°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for an additional 30 minutes
  3. waitleft
  4. washwashed once with water, twice with saturated aqueous sodium bicarbonate solution and once with saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ac2f3f24dfe54c2b8418d4d430304963
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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