(2-Benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine → (2-Benzenesulfonyl-1-ethyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine
Reaction equation
[C:1]1([S:7]([N:10]2[C:25]([CH:26]=[CH2:27])=[C:14]3[CH2:15][CH:16]([N:22]([CH3:24])[CH3:23])[C:17]4[CH2:18][O:19][CH:20]=[CH:21][C:12]([C:13]=43)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.O1CCCC1.[Pd]>[C:1]1([S:7]([N:10]2[C:25]([CH2:26][CH3:27])=[C:14]3[CH2:15][CH:16]([N:22]([CH3:23])[CH3:24])[C:17]4[CH2:18][O:19][CH:20]=[CH:21][C:12]([C:13]=43)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
Compound (54) 200.1 mg was dissolved in a mixture of methanol 8 ml and tetrahydrofuran 4 ml. 10% Pd/C 49.8 mg was added. The mixture was stirred under hydrogen atmosphere for 18 h at room temperature. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform:hexane (1:1) to give the titled compound as a colorless oil 198 mg. Yield 98%. This was treated with 1 eq. of oxalic acid to give the salt, which was recrystallized from ether-methanol to give colorless crystals, m.p. 193-194° C.(dec.).
Workup
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue obtained
- customwas chromatographed on aluminum oxide in chloroform:hexane (1:1)
Sources & evidence
- ORD record
- ord-67d1fc3341364fea8a330c8d32f64ba3
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858640B2
Reaction notes
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