Ammonia → 2,3,5,6-Tetrahydrobenzo[b][1,5]diazocin-4(1H)-one
Reaction equation
[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.I[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][NH2:24].N>O.[Cu]I.C1(C)C=CC=CC=1>[NH:1]1[CH2:4][CH2:3][C:2](=[O:5])[NH:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]1=2Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 2-azetidinone (86 mg, 1.21 mmol), K3PO4 (430 mg, 2.03 mmol), evacuated, and backfilled with Ar. N,N′-Dimethylethylenediamine (11 μL, 0.103 mmol, 10 mol %), 2-iodobenzylamine (132 μL, 1.00 mmol), and toluene (1 mL) were added under Ar. The Schlenk tube was sealed and the reaction mixture was stirred at 100° C. for 22 h. The resulting suspension was allowed to reach room temperature, poured into a solution of 30% aq ammonia (1 mL) in water (20 mL), and extracted with 3×20 mL CH2Cl2. The combined organic layers were dried (Na2SO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm, ethyl acetate-methanol 10:1, 15 mL fractions). Fractions 10–20 provided 144 mg of the desired product (82% yield) as a white solid.
Workup
- customevacuated
- customThe Schlenk tube was sealed
- customto reach room temperature
- extractionextracted with 3×20 mL CH2Cl2
- dry with materialThe combined organic layers were dried (Na2SO4)
- concentrationconcentrated
- customthe residue was purified by flash chromatography on silica gel (2×15 cm, ethyl acetate-methanol 10:1, 15 mL fractions)
Sources & evidence
- ORD record
- ord-bfe97ac9c924415c92ac7c80b843f2dd
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115784B2
Reaction notes
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