Dichloromethane → HCID 131724526, compound
Reaction equation
C(O[C:4](=O)/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([C:17]([O:19]C(C)(C)C)=O)[CH2:14][CH2:13][CH2:12]2)C.CO[CH2:27][N:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)C[Si](C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:49]>>[ClH:49].[CH2:34]([N:28]1[CH2:27][C@@H:6]2[C@H:5]([C:17](=[O:19])[N:15]3[CH2:14][CH2:13][CH2:12][C:11]4[CH:10]=[CH:9][CH:8]=[C:7]2[C:16]3=4)[CH2:4]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1Participants
Procedure
To a solution of tert-butyl 8-[(1E)-3-ethoxy-3-oxo-1-propenyl]-3,4-dihydro-1(2H) -quinolinecarboxylate (2.55 g, 7.7 mmol) in 50 mL of methylene chloride at 0° C. was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (4.6 g, 19.3 mmol) and trifluoroacetic acid (0.24 mL, 3.1 mmol). The cooling bath was removed and the solution was allowed to stir with warming to ambient temperature for 24 h. The methylene chloride was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (elution with 5:1 hexane/ethyl acetate) to afford 3.0 g (83%) of the title compound as an oil. LRMS (ES)+: 465.3 (M+H)+.
Workup
- customThe cooling bath was removed
- customThe methylene chloride was removed under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with saturated aqueous sodium bicarbonate and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (elution with 5:1 hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-67b2d350e2f9483b9d9c6780a49acaae
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06777406B2
Reaction notes
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