Methanol → HCID 131720619, compound

HRID 1599377Notes

Reaction equation

HRID 1599377 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]=[CH:11][CH:10]=[C:9]([C@H:13]([OH:24])[C@@H:14]3[N:19]4[CH2:20][C@H:21]([CH:22]=[CH2:23])[CH:16]([CH2:17][CH2:18]4)[CH2:15]3)[C:7]=2[CH:8]=1.[CH2:25]([O:27][C:28](=[O:33])[CH2:29][N:30]=[C:31]=[O:32])[CH3:26].CO>ClCCl>[CH2:25]([O:27][C:28](=[O:33])[CH2:29][NH:30][C:31]([O:24][C@@H:13]([C:9]1[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[N:12]=[CH:11][CH:10]=1)[C@@H:14]1[N:19]2[CH2:18][CH2:17][C@H:16]([C@@H:21]([CH:22]=[CH2:23])[CH2:20]2)[CH2:15]1)=[O:32])[CH3:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 5953(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanolHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 131720619HCID 131720619, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 mg (0.61 mmol) of quinidine in 5 ml of dry dichloromethane was added 74 ml (0.65 mmol) of ethylisocyanatoacetate. The mixture was allowed to stir magnetically at room temperature for 18 h and concentrated under reduced pressure. The residue was purified on preparative thin layer chromatography (silica, 2 mm) using a mixture of 1:9 ethyl acetate:methanol as the eluent and yielded 130 mg (0.28 mmol, 46%) of (8). MS, IR and NMR data confirmed identity of the compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified on preparative thin layer chromatography (silica, 2 mm)
  3. additiona mixture of 1:9 ethyl acetate

Sources & evidence

ORD record
ord-e920f15de8cf43719d7f5647b672e6d4
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

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