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CAS No. : | 10314-98-4 | MDL No. : | MFCD01568759 |
Formula : | C14H17NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | URTPNQRAHXRPMP-UHFFFAOYSA-N |
M.W : | 263.29 | Pubchem ID : | 736489 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 73.2 |
TPSA : | 66.84 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.74 cm/s |
Log Po/w (iLOGP) : | 2.25 |
Log Po/w (XLOGP3) : | 1.64 |
Log Po/w (WLOGP) : | 1.59 |
Log Po/w (MLOGP) : | 1.57 |
Log Po/w (SILICOS-IT) : | 1.28 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.41 |
Solubility : | 1.03 mg/ml ; 0.0039 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.66 |
Solubility : | 0.58 mg/ml ; 0.0022 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.36 |
Solubility : | 1.15 mg/ml ; 0.00436 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.59 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
100% | With sodium hydrogencarbonate; sodium carbonate In water; acetonitrile at 0 - 20℃; for 2 h; | To a solution of isonipecotic acid (1.29g, 10 mmol) in a mixture of CH3CN/H2O (2:3, 0.1M), NaHCO3 (1.5eq) and Na2CO3 (1.5 eq) were added (pH~ 10-11). Once the mixture was cooled to 0 °C, Cbz-Cl (1.42 mL,1.7 g, 10 mmol). was slowly added The resulting solution was stirred for 2 h at rt. After completion ofthe reaction, the mixture was acidified by dropwise addition of a 1 N HCl aqueous solution. Then, CH3CNwas removed by evaporation, followed by the extraction with EtOAc (3x). Finally the combined organicphase was washed with brine, dried over Na2SO4, and concentrated to afford the desired product inquantitative yield, which was used in the next reaction without further purification. |
96% | With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; | Stage (i): 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid Water (75 ml) was added to piperidine-4-carboxylic acid (25 g) in THF (75 ml), followed by sodium bicarbonate (30.8 g). The mixture was cooled to 0° C. and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was subsequently stirred at room temperature for 5 h (TLC control). When the reaction was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml), and the mixture was washed with ethyl acetate (2*150 ml). The aqueous phase was rendered acidic with dilute aqueous HCl and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Yield: 48.5 g (96percent) |
96% | With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; | Stage (i): 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid To piperidine-4-carboxylic acid (25 g) in THF (75 ml) there was added water (75 ml) followed by sodium bicarbonate (30.8 g). The mixture was cooled to 0° C., and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was then stirred for 5 hours at room temperature (TLC monitoring). When the reaction was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml) and washed with ethyl acetate (2*150 ml). The aqueous phase was acidified with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Yield: 48.5 g (96percent) |
96% | Stage #1: With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; Stage #2: With hydrogenchloride In water |
To piperidine-4-carboxylic acid (25 g) in THF (75 ml) there was added water (75 ml), followed by sodium bicarbonate (30.8 g). The mixture was cooled to 0° C., and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was then stirred for 5 h at room temperature (TLC monitoring). When the reaction was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml) and washed with ethyl acetate (2.x.150 ml). The aqueous phase was acidified with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated under vacuum. Yield: 48.5 g (96percent) |
96% | With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 25℃; | Water (75 ml), followed by sodium bicarbonate (30.8 g), was added to piperidine-4-carboxylic acid (25 g) in THF (75 ml). The mixture was cooled to 0° C., and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was then stirred for 5 h at room temperature (TLC monitoring). When the conversion was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml) and washed with ethyl acetate (2.x.150 ml). The aqueous phase was acidified with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Yield: 48.5 g (96percent) |
96% | With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; | Step (i): 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid Water (75 ml) was added to piperidine-4-carboxylic acid (25 g) in THF (75 ml), followed by sodium bicarbonate (30.8 g). The mixture was cooled to 0° C. and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was then stirred at room temperature for 5 h (TLC control) When the reaction was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml), and the mixture was washed with ethyl acetate (2*150 ml). The aqueous phase was acidified with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Yield: 48.5 g (96percent) |
96% | Stage #1: With sodium hydrogencarbonate In tetrahydrofuran; water Stage #2: at 0 - 20℃; for 5 h; |
Synthesis of the amine unit AMN-08: 9-Pyridin-4-yloxy)-3- azaspiro[5.5]undecane dihydrochloride (AMN-08); Stage (i): 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid; Water (75 ml) was added to piperidine-4-carboxylic acid (25 g) in THF (75 ml), followed by sodium bicarbonate (30.8 g). The mixture was cooled to 0 0C and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was then stirred at room temperature for 5 h (TLC control).. When the reaction was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml), and the mixture was washed with ethyl acetate (2 x 150 ml). The aqueous phase was acidified with dilute aqueous HCI solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Yield: 48.5 g (96 percent) |
91% | With potassium carbonate In 1,4-dioxane; water at 0 - 20℃; | To a solution of piperidine-4-carboxylic acid in a 1:1 mixture Of H2O/ dioxane (0.4 M), 5 eq OfK2CO3 were added before dropwise introduction at 0 °C of 1.1 eq of benzyl chloroformate. The reaction was stirred at RT overnight. The reaction was first washed with Et2O. The aqueous phase was acidified to pH 2 with aqueous HCl (6N) before being extracted with EtOAc (3x). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the product (91 percent); MS (ES+) m/z 264 (M+H)+ |
72% | With sodium hydrogencarbonate In water at 20℃; for 20 h; | To an aqueous solution (i.e., 300 ml of distilled water) of isonipecotic acid (10.0 g, 77.4 mmol) and sodium bicarbonate (19.5 g, 232 mmol) was added benzyl chloroformate (11.5 ml, 80.9 mmol). The reaction solution was stirred at room temperature for 20 hours, and ethyl acetate was added thereto then the solution was separated. Concentrated hydrochloric acid was added to the aqueous layer to bring a pH level to 1, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under a reduced pressure to give a title compound (14.7 g, 55.8 mmol, 72percent) as a colorless oil product. 1H-NMR (400 MHz, CDCl3) δ: 1.69 (2H, m), 1.93 (2H, m), 2.51 (1H, m), 2.96 (2H, m), 4.11 (2H, m), 5.13 (2H, s), 7.29-7.39 (5H, m). |
71% | With sodium hydrogencarbonate In diethyl ether | (1) A diethyl ether (50 ml) solution of benzyl chloroformate (36 g, 0.21 mols) was dropwise added to an aqueous solution (200 ml) of isonipecotic acid (25 g, 0.19 mols) and sodium hydrogencarbonate (49 g, 0.58 mols) with stirring at room temperature. After the addition, this was further stirred at room temperature for 15 hours. The reaction mixture was acidified with concentrated hydrochloric acid added thereto, and then extracted with ethyl acetate. The extract was washed with brine, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from isopropyl ether/hexane, and taken out through filtration. A colorless crystal of N-benzyloxycarbonylisonipecotic acid (36 g, 71 percent) was obtained. m.p. 79-80°C 1H-NMR (CDCl3) δ: 1.57-1.77(2H,m), 1.90-1.96(2H,m), 2.45-2.59(1H,m), 3.89-3.03(2H,m), 4.06-4.13(2H,m), 5.13(2H,s), |
64% | With sodium hydroxide In water; toluene at 0 - 20℃; for 6.5 h; Alkaline aqueous solution | To a stirred solution of pipehdine-4-carboxylic acid (5.0 g, 38.7 mmol) and NaOH (1.86 g, 46.5 mmol) in H2O (15 ml) was added dropwise a 50percent solution of benzyl chloroformate in toluene (13.6 ml_, 40.6 mmol) over a period of half an hour at 0 °C. The reaction mixture was stirred at room temperature for 6 hours. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was acidified with dil. HCI (pH 3) and extracted with ethyl acetate (3x100 ml). The combined organic phases were dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography (silica gel, elution with 30percent ethyl acetate/n- hexanes) to afford piperidine-1 ,4-dicarboxylic acid monobenzyl ester (Vl) (6.5 g, 64percent) as a pale yellow oil.HPLC purity λ = 220 nm: 95percent. ESMS: m/z = 264 (M+1 ). |
86% | With sodium hydrogencarbonate In water; ethyl acetate; toluene | STR76 Step A: N-CBZ-isonipecotic acid Benzyl chloroformate (16.4 mL, 115 mmol) in toluene (50 mL) was added dropwise to a stirred solution of 12.9 g (100 mmol) of isonipecotic acid (Aldrich) and 21.0 g (250 mmol) of sodium bicarbonate in 200 mL of water. After 14 h, the mixture was extracted with ether (3*50 ml) and the ether layers were discarded. The aqueous layer was acidified with conc. HCl to pH 2, causing the product to precipitate. The product was partitioned into ethyl acetate (3*50 mL) and the combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to yield 22.6 g (86percent) of N-CBZ-isonipecotic acid as a viscous oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide In water at 0 - 25℃; for 18 h; | Example SA 2-[(PIPERIDINE-4-CARBONYL)-AMINO]-PROPIONIC acid tert-butyl ester A solution of isonipecotic acid (25 g, 194 mmol) in 3 N NaOH (130 mL) at 0°C was treated with CbzCl over 15 min with vigorous stirring. Then the reaction mixture was stirred at ambient temperature for 18 h and partitioned with diisopropyl ether (2x250 mL). The aqueous layer was separated, made acidic with 4 N HC1, and extracted with EtOAc (2x250 mL). The combined organic layers were dried (MGS04), filtered and concentrated under reduced pressure to provide piperidine-1, 4-dicarboxylic acid monobenzyl ester (40.2 g) as a clear colorless viscous oil. A portion of this material (26.5 g, 100 mmol) in THF (100 mL) was treated with DMF (5 drops) followed by dropwise addition of oxalyl chloride (8.67 mL, 100 mmol). When the evolution of gas had ceased the mixture was stirred for an additional 30 min and concentrated under reduced pressure. The residue obtained was evaporated from toluene (1X75 mL). The resulting acid chloride was dissolved in THF (220 mL) and treated with (L)-ALANINE-TERT-BUTYL ester HC1 salt (18.2 g, 100 mmol) and N, N-diisopropyl- ethylamine (52 mL, 300 mmol) at 0°C. The mixture was warmed to ambient temperature and stirred for two hours. To this DMAP (240 mg, 1.90 mmol) was added in one portion and the resulting white sus- pension was stirred for 65 h. The reaction mixture was quenched with 4 M HC1 and partitioned with EtOAc. The organic phase was separated, washed with a solution of aqueous NAHC03 followed by brine, dried (MGS04), filtered and concentrated under reduced pressure to provide 4- (L-TERT-BUTOXYCARBONYLETHYL- CARBAMOYL)-PIPERIDINE-L-CARBOXYLIC acid benzyl ester. This was subjected to hydrogenolysis next.;Example 11F PIPERIDINE-1, 4-DICARBOXYLIC acid monobenzyl ester A 2000 mL flask was charged with isonipecotic acid (100 g, 776 mmol) and 3 N NaOH (550 mL), and was cooled with an ice bath to 14°C (internal temperature). CbzCl (145 mL) was added dropwise and the temperature gradually rose to 25°C during the addition over 20 min. The mixture was vigorously stirred and the cooling bath removed. The mixture was stirred overnight and the next morning poured directly into a 2 L sep. funnel and extracted with diisopropyl ether (2XLOOOML). The aqueous layer was acidified with 4 N HC1, extracted with EtOAc (2X1000 mL), dried over MGSO4, filtered and concentrated affording 210 g of acid, as a clear colorless viscous oil which was crystallized upon cooling. This was dried to provide the title compound (208 g, 100percent). LH NMR (400 MHz, DMSO-d6) 10.67 (s, 1H), 7.42-7. 30 (m, 5H), 5.13 (s, 2H), 4.08-4. 02 (m, 2H), 3.10-2. 89 (m, 2H), 2.5 (m, 1H), 1.94-1. 89 (m, 2H), 1.621. 52 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With sodium carbonate In water; acetonitrile at 20℃; for 16 h; | To a solution of piperidine-4-carboxylic acid (10.0 g, 77.4 mmol) and Na2CO3 (8.21 g, 77.4 mmol) in water (100 mL) was added a solution of benzyl 2,5-dioxopyrrolidin-1-yl carbonate (19.3 g, 77.4 mmol) in MeCN (100 mL). The reaction was stirred at ambient temperature for about 16 h and then concentrated under reduced pressure. The resulting aqueous solution was quenched with NH4Cl and was then extracted with EtOAc (2.x.100 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid as a white solid (4.56 g, 22percent): LC/MS (Table 2, Method a) Rt=1.93 min; MS m/z: 262 (M-H)-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: for 5 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In water |
To a solution of 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid (Reference Example 27) (540 mg, 2.05 mmol) in methanol was added concentrated sulfuric acid (two drops with a Pasteur pipette), and the resultant was heated under reflux for 5 hours. The reaction solution was cooled to room temperature and then concentrated under a reduced pressure. Saturated aqueous sodium bicarbonate was added to the residue, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure to give a title compound (532 mg, 1.92 mmol, 93percent) as a colorless oil product. 1H-NMR (400 MHz, CDCl3) δ: 1.57-1.73 (2H, m), 1.82-1.96 (2H, m), 2.43-2.55 (1H, m), 2.85-2.97 (2H, m), 3.69 (3H, s), 4.02-4.17 (2H, m), 5.12 (2H, s), 7.29-7.40 (5H, m). IR (neat, cm-1): 1732, 1696, 1450, 1433, 1223, 1192, 1175, 1040. |
67% | at 0℃; Reflux | Stage (ii): 1-Benzyl 4-methyl piperidine-1,4-dicarboxylate 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0° C. and thionyl chloride (13.34 ml) was added dropwise. The mixture was subsequently refluxed for 20 min (TLC control). When the reaction was complete, the methanol was distilled off, the residue was taken up in water (15 ml) and with ethyl acetate (2*150 ml). The combined organic phases were extracted with water and sat. sodium chloride solution and the extract was dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67percent) |
67% | at 0℃; Reflux | Stage (ii): 1-Benzyl 4-methyl piperidine-1,4-dicarboxylate 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0° C., and thionyl chloride (13.34 ml) was added dropwise. The mixture was then refluxed for 20 minutes (TLC monitoring). When the reaction was complete, the methanol was distilled off and the residue was taken up in water (15 ml) and with ethyl acetate (2*150 ml). The combined organic phases were extracted with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67percent) |
67% | at 0℃; Reflux | 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0° C., and thionyl chloride (13.34 ml) was added dropwise. The mixture was then refluxed for 20 min (TLC monitoring). When the reaction was complete, the methanol was distilled off and the residue was taken up in water (15 ml) and with ethyl acetate (2.x.150 ml). The combined organic phases were extracted with water and sat. sodium chloride solution, dried (Na2SO4) and concentrated under vacuum. Yield: 38 g (67percent) |
67% | at 0℃; Reflux | 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0° C., and thionyl chloride (13.34 ml) was added dropwise. The mixture was then refluxed for 20 min. (TLC monitoring). When the conversion was complete, the methanol was distilled off and the residue was taken up in water (15 ml) and extracted with ethyl acetate (2.x.150 ml). The combined organic phases were extracted with water and sat. sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67percent) |
67% | at 0℃; Reflux | Step (ii): 1-Benzyl 4-methyl piperidine-1,4-dicarboxylate 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0° C. and thionyl chloride (13.34 ml) was added dropwise. The mixture was then refluxed for 20 min (TLC control). When the reaction was complete, the methanol was distilled off, the residue was taken up in water (15 ml) and with ethyl acetate (2*150 ml). The combined organic phases were extracted with water and sat. sodium chloride solution and the extract was dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67percent) |
67% | for 0.333333 h; Reflux | Stage (ii): 1 -Benzyl 4-methyl piperidine-1,4-dicarboxylate; 1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0 0C and thionyl chloride (13.34 ml) was added dropwise. The mixture was then refluxed for 20 min (TLC control). When the reaction was complete, the methanol was distilled off, the residue was taken up in water (15 ml) and extracted with ethyl acetate (2 x 150 ml). The combined organic phases were extracted with water and sat. sodium chloride solution and the extract was dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67 percent) |
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