Triphenylarsine → 3-Hexyl-6-methyl-6-[3-(2-thienyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one
Reaction equation
C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Sn](CCCC)(CCCC)[C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)CCC.[CH2:38]([N:44]1[CH2:49][CH:48]2[CH:46]([C:47]2([C:51]2[CH:56]=[CH:55][CH:54]=[C:53](I)[CH:52]=2)[CH3:50])[C:45]1=[O:58])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:38]([N:44]1[CH2:49][CH:48]2[CH:46]([C:47]2([CH3:50])[C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[CH:52]=2)[C:45]1=[O:58])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To tris(dibenzylideneacetone)dipalladium (0) (4.5 mg, 4.91 lmol) in tetrahydrofuran (1 ml) at room temperature was added triphenylarsine (5.9 mg, 19.2 μmol). After 5 min, 2-(tributylstannyl)thiophene (0.10 g, 0.27 mmol) in tetrahydrofuiran (1 ml) was added followed by 3-hexyl-6-(3-iodophenyl)-6-methyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 67, 78 mg, 0.19 mmol) in tetrahydrofuran (1 ml). The reaction mixture was stirred at room temperature for 16 h and then refluxed for 2 h. The cooled reaction mixture was concentrated in vacuo and chromatographed on silica gel eluting with hexane:ethyl acetate (2.1) to give the title compound as a colourless oil (68 mg, 98%).
Workup
- temperaturerefluxed for 2 h
- customThe cooled reaction mixture
- concentrationwas concentrated in vacuo
- customchromatographed on silica gel eluting with hexane
Sources & evidence
- ORD record
- ord-317aa37c4dd7487c81077c2c4dea575b
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313312B1
Reaction notes
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