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EXAMPLE 42E; 1-tert-butyl 4-ethyl azepane-1,4-dicarboxylate A solution of example 42D (0.54 g, 2.0 mmol) in 20 ml of MeOH was treated with 10percent Pd/C (50 mg) under hydrogen overnight. Solid material was filtered off and the filtrate was concentrated. The residue was purified by flash column chromatography (20percent EtOAc in hexane) to give the title product (310 mg, 55percent yield). MS (DCI/NH3) m/z 272 (M+H)+.
With lithium diisopropylamide; In tetrahydrofuran; at -78 - -20℃; for 3.0h;
EXAMPLE 42F; 1-tert-butyl 4-ethyl 4-methylazepane-1,4-dicarboxylate A solution of Example 42E (1.7 g, 6.27 mmol) and iodomethane (0.8 ml, 12.55 mmol) in THF (15 mL) was treated with LDA (2.0 M solution in THF, 6.3 mL, 12.55 mmol) at -78 C. under nitrogen. The temperature of the cooling bath was slowly raised to -20 C. within 1 h and the mixture was stirred at the same temperature for additional 2 h. After quenching with water, the mixture was partitioned between water and EtOAc. The organic phase was washed with water and concentrated. The residue was purified by flash chromatography (20-40% EtOAc in hexane) to give the title product (1.2 g, 67% yield). MS (DCI/NH3) m/z 286 (M+H)+.
With hydrogen;palladium 10% on activated carbon; In methanol;
EXAMPLE 42E; 1-tert-butyl 4-ethyl azepane-1,4-dicarboxylate A solution of example 42D (0.54 g, 2.0 mmol) in 20 ml of MeOH was treated with 10% Pd/C (50 mg) under hydrogen overnight. Solid material was filtered off and the filtrate was concentrated. The residue was purified by flash column chromatography (20% EtOAc in hexane) to give the title product (310 mg, 55% yield). MS (DCI/NH3) m/z 272 (M+H)+.
Di-tert-butyl dicarbonate was added to a chloroform solution of ethyl 7-azepane-4-carboxylate under ice-cooling, and stirred overnight at room temperature, and the solvent was evaporated to obtain <strong>[912444-90-7]1-tert-butyl-4-ethyl azepane-1,4-dicarboxylate</strong>. The compound was dissolved in methanol, and hydrolyzed with potassium hydroxide (1.0 equivalent) in methanol to obtain 1-(tert-butoxycarbonyl)azepane-4-carboxylic acid. FAB-MS(M+H)+: 244.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 0.5h;Cooling with ice;
1-tert-Butyl 4-ethyl azepane-l,4-dicarboxylate (3.3 g, 12 rnmol, USPublication No. 2006/229289) was dissolved in THF (100 mL) and cooled in an ice bath. LiAlH4 (12 mL, 12 mmol) was added slowly and stirred for 30 minutes. Water (~3 mL) was added slowly, followed by Na2SO4. The reaction was filtered and concentrated to afford crude tert-butyl 4-(hydroxymethyl)azepane-l -carboxylate (2.8 g, 100%).
95%
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2.0h;Inert atmosphere;
tert-butyl 4-(hydroxymethyl)azepane-1-carboxylateInto a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of <strong>[912444-90-7]1-tert-butyl 4-ethyl azepane-1,4-dicarboxylate</strong> (1.00 g, 3.69 mmol, 1.00 equiv) and tetrahydrofuran (20 mL) with stirring at 0 C., to which was added LiAlH4 (170 mg, 4.48 mmol, 1.20 equiv). The resulted solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 10 mL of water/ice. The solids were filtered out. The filtrate was extracted with ethyl acetate (20 mL×3). The organic phase was washed with 1×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluted with ethyl acetate and petroleum ether (1:3). This resulted in 800 mg (95%) of tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate as yellow oil. 1H NMR (300 MHz, DMSO-d6): delta 4.49 (t, J=5.4 Hz, 1H), 3.33-3.44 (m, 2H), 3.12-3.23 (m, 4H), 1.72-1.81 (m, 3H), 1.39 (br, 11H), 1.16-1.20 (m, 1H), 0.91-1.08 (m, 1H).
With palladium 10% on activated carbon; hydrogen; In methanol; under 760.051 Torr; for 3.0h;
General procedure: To a mixture of (E)-1-tert-butyl 3-methyl 3-styrylazetidine-1,3-dicarboxylate (500 mg, 1.58 mmol) and PdC(100 mg, 10%) in methanol (30 mL) was bubbled withhydrogen (1 atm) for 3 h. Upon completion of the reaction,the reaction mixture was filtered and the filtrate was concentratedto afford 500 mg of 1-tert-butyl 3-methyl 3-phenethylazetidine-1 ,3-dicarboxylate, which was used directlyfor the next step without further purification. LC-MS (ESI +):mlz 342 [M+Nat.
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