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CAS No. : | 162504-75-8 | MDL No. : | MFCD02179013 |
Formula : | C14H25NO4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | RWDYQFGCHAJYOJ-UHFFFAOYSA-N |
M.W : | 271.35 | Pubchem ID : | 1502093 |
Synonyms : |
|
Chemical Name : | Methyl N-Boc-4-piperidinepropionate |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of tert-butyl 4- (3-METHOXY-3-OXOPROPYL) PIPERIDINE-1-CARBOXYLATE (2.0 g, 7.37 mmol) in 8 ml of methanol was added a solution of LIOH monohydrate (0.46g, 11.0 mmol) in 2 ml of water. The resulting solution was stirred at rt for 16h and it was concentrated under vacuum. To the residue was added 0.35 ml of acetic acid and 0.1 ml of water. The mixture was poured into a solution of EtOAc and CH2CL2 (1 : 1). The organic layer was dried with NA2SO4, filtered through celite and concentrated. To give 1.6g of 3- [1- (tert-butoxycarbonyl) piperidin-4- yl] propanoic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen;palladium 10% on activated carbon; In methanol; under 2585.81 Torr; for 15h; | To a solution of the compound of Step 2 (3.38 g, 12.6 mmol) in 50 ml of methanol was added lg of 10% Pd/C and the mixture was hydrogenated at 50 psi of H2 on Parr apparatus for 15 h. The mixture was filtered through celite and concentrated to afford 3. 11G of tert-butyl 4- (3- methoxy-3-oxopropyl) PIPERIDINE-1-CARBOXYLATE. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; | INTERMEDIATE 16 Step A: Iodomethane (556YL, 8. 93MMOL) was added dropwise to A cooled (0C) mixture of commercially available 3- [1- (tert-butoxycarbonyl) piperidin-4-yl] propanoic acid (2.09g, 8. 12mmol) and K2CO3 (2.81g, 20. 3MMOL) in 20ML of DMF. The reaction mixture was permitted to warm to rt and stir overnight. The reaction mixture was diluted with ether and washed four times with water, then once with brine. The ethereal layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by MPLC (silica, 40% ethyl acetate/hexanes) provided tert-butyl 4- (3-METHOXY-3-OXOPROPYL) PIPERIDINE-L- carboxylate. | |
With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; | Step A Iodomethane (556 muL, 8.93 mmol) was added dropwise to a cooled (0 C.) mixture of commercially available <strong>[154775-43-6]3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoic acid</strong> (2.09 g, 8.12 mmol) and K2CO3 (2.81 g, 20.3 mmol) in 20 mL of DMF. The reaction mixture was permitted to warm to rt and stir overnight. The reaction mixture was diluted with ether and washed four times with water, then once with brine. The ethereal layer was dried over anhydrous MgSO4, filtered, and concentrated. Purification by MPLC (silica, 40% ethyl acetate/hexanes) provided tert-butyl 4-(3-methoxy-3-oxopropyl)piperidine-1-carboxylate: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1) (+-)-cis-N1-[3-[1-(tert-Butoxycarbonyl)piperidin-4-yl]propionyl]-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine was obtained from <strong>[162504-75-8]1-(tert-butoxycarbonyl)-4-[2-(methoxycarbonyl)ethyl]piperidine</strong> (J. Med. Chem., 1998, Vol. 41, p. 2492) in a similarmanner to the step 1) of Example 83. 1H-NMR (CDCl3) delta: 1.00-1.17(2H,m), 1.30-1.80(11H,m), 1.44(9H,s), 1.80-1.95(1H,m), 2.10-2.23(1H,m), 2.29(2H,t,J=7.8Hz), 2.50-2.70(2H,m), 3.90-4.18(3H,m), 4.23(1H,br.s), 6.05(1H,br,J=6.0Hz), 6.85(1H,d,J=2.0Hz), 7.22(1H,dd,J=8.8,1.8Hz), 7.37(1H,d,J=8.8Hz), 7.62(1H,d,J=1.8Hz), 7.89(1H,br.s), 9.59(1H,s). MS (ESI) m/z: 531(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
205 mg (97%) | Step D: (3-(1-t-Butoxycarbonylpiperidin-4-yl)propanoic acid, methyl ester A solution of 200 mg (0.79 mmol) of (3-(1-t-butoxycarbonylpiperidin-4-yl)propanoic acid (from EXAMPLE 98, Step C) in 2 mL of 1:1 v/v MeOH/THF was treated with a 2 M trimethylsilyl-diazomethane solution in THF until a yellow color persisted. After stirring the mixture at rt for 1 h, the solution was concentrated and the residue purified by column chomatography on 15 g silica gel with a gradient of 0-25% acetone/hexanes (v/v) to give 205 mg (97%) of the title compound: 1H NMR (500 MHz) delta 1.11 (dq,J=4.3,8.3,2H). 1.38-1.44 (m, 1H), 1.46(s,9H), 1.59 (q, J=7.5, 2H), 1.65 (d, J=13.3, 2H), 2.35 (t, J=7.6, 2H), 2.62-2.73 (2H), 3.68 (s, 3H), 4.09 (bs, 2H). |
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