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CAS No. : | 32811-76-0 | MDL No. : | MFCD20040367 |
Formula : | C7H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ASZRODBLMORHAR-UHFFFAOYSA-N |
M.W : | 144.17 | Pubchem ID : | 520596 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.1 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.96 cm/s |
Log Po/w (iLOGP) : | 1.82 |
Log Po/w (XLOGP3) : | 0.31 |
Log Po/w (WLOGP) : | 0.32 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 0.61 |
Consensus Log Po/w : | 0.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.8 |
Solubility : | 23.0 mg/ml ; 0.16 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.85 |
Solubility : | 20.4 mg/ml ; 0.141 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.28 |
Solubility : | 74.8 mg/ml ; 0.519 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
78% | With methanol; sodium tetrahydroborate; at 0℃; for 0.5h; | Step 1: 3-Hydroxy-cyclopentanecarboxylic acid methyl ester A solution of 3-oxo-cyclopentanecarboxylic acid methyl ester (2.0 g, 1.0 eq) was dissolved in methanol (15 mL) and cooled to 0 C. NaBH4 (0.53 g) was added and the mixture was stirred at 0 C. for 30 min. The mixture was quenched with acetic acid (0.5 mL) and the methanol was evaporated. The residue was taken up in ethyl acetate, washed with water, dried and evaporated. Purification by flash chromatography on silica gel with a dichloromethane/ethyl acetate gradient yielded the title compound as mixture of the cis and trans isomers. Colorless liquid, 1.6 g, 78%. |
70.0% | With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20℃; for 12h; | Methyl 3-oxocyclopentane- I -carboxylate (1.0 gm, 7.04 mmoi, 1.0 eq) was dissolved in THF (10 mL) and the mixture was cooled to 0 C. Then sodium borohydride (0.32 gIn, 8.45 mmol, 1.2 eq) was added and the mixture was stirred for 12 h. Duringstirring, temperature of the system gradually allowed to increase to ambient temperature. After completion consumption of the starting material, the mixture was quenched with saturated aq. amrnonium chloride (10 mL). The mixture was then extracted with ethyl acetate (2 x 10 rnL). The organic extract was separated, dried over anhydrous Na2SO4 filtered and solvents evaporated from the filtrate to obtain a crude residue. The crude residue obtained was purified by column chromatography on silica gel, 100-200 mesh, using 0-25% gradient of ethyl acetate in hexane as eluent. The fractions with the desiredproduct were concentrated to obtain the title product as a colourless liquid (0.7 grn,70.0%). ELSD-MS: Purity 98.23%. MS calculated for [Ml 14408 and found [M+H]t14500. ?H NMR (400MHz, CDC13): oe 431 (bs, IH), 3.703.67 (m, 3H), 289-2.79 (rn, IH), 2.09-1.74 (m, 6H). |
68% | With sodium borohydrid; In tetrahydrofuran; | Methyl 3-hydroxycyclopentanecarboxylate STR1069 A solution of methyl 3-oxocyclopentanecarboxylate (9.58 g, 67.5 mmol) in THF (100 ml) was added to a slurry of sodium borohydride (3.8 g, 100 mmol) in THF (100 ml). The mixture was stirred at 23 C. for 2 h, cooled to 0 C. and acidified to pH 6 with 1M hydrochloric acid. The mixture was extracted with EtOAc (2*100 ml) and the organic extracts were washed with water and saturated sodium chloride (100 ml each). The extracts were dried and the solvent was evaporated in vacuo to give the title compound as a colorless liquid, 6.66 g (68% yield), (a mixture of two isomers); ir (liq.) numax: 3450, 1725 cm-1: 1 Hmr (CDCl3) delta: 4.30 (m, 1H, H-3), 3.70-3.67 (2*s, 3H, OMe), 2.9 (m, 1H, H-1), 2.8 (s, 1H, OH) and 2.3-1.6 ppm (m, 6H, CH2). |
61% | With sodium tetrahydroborate; In methanol; at 0℃; for 1h; | To a solution of methyl 3-oxocyclopentanecarboxylate (5.0 g, 35.2 mmol, 1.0 eq) in MeOH (10 mL) was slowly added NaBH4 (2.0 g, 52.8 mmol, 1.5 eq) at 0 C. Then the mixture was stirred at 0 C for 1 h. The reaction was quenched with H20 (5 mL). The mixture wasextracted with DCM (30 mL x 3). The combined organics were dried over Na2SO4, filtrated and concentrated. The residue was purified by silica gel chromatography (PE/EA = 4/1) to give methyl 3-hydroxycyclopentanecarboxylate (3.1 g, Y: 61%) as a white solid. ESI-MS (M+H):145.1. |
55% | With sodium tetrahydroborate; In methanol; at 0℃; for 0.5h; | To a solution of methyl 3-oxocyclopentanecarboxylate (1.0 g, 7.0 mmol) in methanol (10 ml) at 0 C was addedSodium borohydride (260 mg, 7.0 mmol) was added and reaction was continued for 30 minutes at this temperature. A small amount of glacial acetic acid was added to the reaction system to quench the reaction and concentrated under reduced pressure to remove the solvent. Ethyl acetate was added to the residue to dissolve the residue, which was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated to give the title compound (558 mg, 55%). |
43% | With sodium hydride; In methanol; at 0℃; for 0.5h; | The <strong>[32811-75-9]methyl 3-oxocyclopentane-1-carboxylate</strong> (4 A) (3.0 g, 21 mmol) dissolved in methanol (30 ml) in, 0 C batch adding sodium borohydride (1.2 g, 32 mmol), continue to reaction 30 minutes. The reaction solution by adding water (50 ml), for 50 ml ethyl acetate (50 ml × 2) extraction, the combined organic phase, the organic phase with saturated salt water (30 ml × 1) washing, drying with anhydrous sodium sulfate, filtered, the filtrate concentrated under reduced pressure to obtain the title compound 3 - hydroxy cyclopentyl carboxylic acid methyl ester (4 B), colorless oily matter (1.3 g, yield 43%). |
With sodium tetrahydroborate; ethanol; at 0 - 20℃; | Intermediate A-11: methyl S-hydroxycyclopentanecarboxylate -step a7 Sodium borohydride (442.6 mg, 11.70 mmol) was added portionwise to a solution of methyl 3-oxocyclopentane-carboxylate A-10 (1.66 g, 11.70 mmol) in absolute ethanol (42.0 mL) at 0 0C. The reaction mixture was allowed to warm to room temperature and stirred for 90 mins, then quenched slowly with a 1 N aqueous solution of hydrogen chloride (10 mL), and concentrated to ca. 15 mL under reduced pressure. The aqueous layer was extracted with methylene chloride (3 x 50 ml_); the combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure to give crude methyl 3-hydroxycyclopentanecarboxylate A- 11 as a yellow oil (1.33 g, Yield=79%). This material was used for next step without purification. MS (ESI), [M+1f 145. | |
With methanol; sodium tetrahydroborate; at 0℃; for 1h; | In a 25 mL round-bottomed flask, methyl 3-oxocyclopentanecarboxylate (0.25 g, 0.22 mL, 1.76 mmol) was dissolved in 5 mL MeOH and cooled to 0 C. NaBH4 (0.07 g, 1.76 mmol) was added and the reaction was stirred at 0 C. for 1 hr. The reaction was quenched with 1 N HCl and the product was extracted with EtOAc (3*20 mL). The organic layers were combined, washed with brine (2*15 mL), and evaporated in 1H NMR (500 MHz, CDCl3-d) 6 ppm 4.46 (tt, J=5.3, 2.7 Hz, 0.34H) 4.33 (tt, J=5.5, 3.0 Hz, 1H) 3.71 (s, 3H) 3.68 (s, 1.3H) 3.12-3.05 (m, 0.3H) 2.89 (tdd, J=9.2, 6.5, 4.5 Hz, 1H) 2.18-1.60 (m, 8H). 3:1 diastereomer ratio. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With trichlorophosphate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aus Keton 2; | ||
2-Methyl-but-2-en, B2H6, Methylcyclopent-3-en-carboxylat; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH / Hydrolysis 2: dibutyl phthalate / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH / Hydrolysis 2: Ag2O / Erhitzen des Reaktionsprodukts mit wss. NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH / Hydrolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: aqueous NaOH / Hydrolysis 2: Ag2O / Erhitzen des Reaktionsprodukts mit wss. NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triethylamine In dichloromethane | 98 Methyl 3-methanesulfonyloxycyclopentanecarboxylate STR1070 Methyl 3-methanesulfonyloxycyclopentanecarboxylate STR1070 A solution of methanesulfonyl chloride (4.7 ml, 60 mmol) in 25 ml of CH2 Cl2 was added dropwise with stirring to a solution of methyl 3-hydroxycyclopentanecarboxylate (6.5 g, 45 mmol) and triethylamine (9.0 ml, 65 mmol) in CH2 Cl2 (65 ml) at 0° C. The solution was stirred at 23° C. for 24 h and then washed with water (3*50 ml). The washes were extracted with CH2 Cl2 and the combined organic extracts were dried, treated with charcoal and filtered. The solvent was evaporated in vacuo to give the title compound as a yellow liquid, 9.1 g (91% yield), and as a mixture of isomers: ir (liq.) νmax: 1730 cm-1; 1 Hmr (CDCl3) δ: 5.13 (m, 1H, H-3), 3.68 (2 Xs, 3H, CO2 Me), 3.00 (s, 3H, SO3 Me), 2.8 (m, 1H, H-1) and 2.4-1.7 ppm (m, 6H, CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; In toluene; at 20℃; for 12h; | Intermediate A-12: methyl 3-(5-bromopyridin-2-yIoxy)cyclopentane carboxylate -step a8A solution of methyl S-hydroxycyclopentanecarboxylate A-11 (500.0 mg, 3.00 mmol) in anhydrous toluene (10.0 ml_) was added to a solution of 5- bromopyridin-2-ol (522.0 mg, 3.00 mmol) in anhydrous toluene (10.0 ml_) at room temperature. Diisopropyl azodicarboxylate (1.57 g, 6.00 mmol) was then added dropwise, and the yellow-orange solution was stirred at room temperature for 12 h. The reaction mixture was then quenched with methanol (1.0 ml_) and concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient) to give methyl 3-(5-bromopyridin-2~yloxy)cyclopentane carboxylate A-12 (462.0 mg, Yield=51%). MS (ESI), [M+Naf 321 , 323. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In dichloromethane at 0 - 20℃; for 4h; | 12.3 Step 3: Synthesis of Methyl 3-((methylsulfonyl)oxy)cyclopentane4-.carboxylate: Methyl 3hydroxycyciopentane-1-carboxylate (0.7 gm, 486 mmol, 1.0 eq) was dissolved in DCM (10 mL) and the solution was cooled to 0 °C. Then methanesulfonyl chloride (0.56 mL, 7.29 mrnol, 1.5 eq) and triethyl amine (2.0 mL, 14.58 mmol, 3.0 eq) were added and the mixture was stirred for 4 h, during which, the temperature was allowed to rise from 0 °C to ambient temperature. After complete consumption of startingmaterial, reaction mixture was diluted with water (10 mL) and extracted with DCM (2 x10 mL). The organic extract was separated, dried over anhydrous Na2SO4, filtered and solvents evaporated from the filtrate under reduced pressure. The crude residue obtained was purified by column chromatography on silica gel, 100-200 mesh, using 0-25% gradient of FtOAc in hexanes as eluent, The fractions containing the desired product wereconcentrated to obtain the title product as colorless liquid (070 gm, 700%). ‘H NMR (400MHz, CDCI3): ö 5.15 (s. 11-1), 3.70 (s. 3H), 3.0 (s. 3H), 2.86-277 (m. 1H), 2.34-186 (in, 6H). |
64% | With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 43.1 Step 1: Preparation of Intermediate 44-1 Methyl 3-hydroxycyclopentane-1-carboxylate (200 mg, 1.4 mmol) and TEA (210 mg, 2.1 mmol) were dissolved in dichloromethane (10 mL),To the reaction mixture was added MsCl (175 mg, 1.5 mmol) with stirring at 0 degrees and stirring was continued at room temperature for 1 hour. The reaction mixture was quenched with ice water and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, then filtered and concentrated to obtain a crude product, which was purified by silica gel column chromatography to obtain a colorless oilMethyl 3-((methylsulfonyl)oxy)cyclopentane-1-carboxylate (Intermediate 44-1, 197 mg, 64% yield). |
With triethylamine In dichloromethane at -20℃; for 0.333333h; | 43.2 Step 2: 3-Methanesulfonyloxy-cyclopentanecarboxylic acid methyl ester A solution of 3-hydroxy-cyclopentanecarboxylic acid methyl ester (1.6 g, 1.0 eq, cis/trans-mixture from step 1) in dichloromethane (25 mL) was cooled to -20° C. and treated with triethylamine (1.4 g, 1.3 eq) and methansulfonyl chloride (1.5 g, 1.2 eq). The mixture was stirred at -20° C. for 20 min and then partitioned between water and dichloromethane. The organic phase was washed with brine, dried over sodium sulfate and evaporated. The title compound was obtained as a yellow liquid (2.4 g, 97%) and was used crude in the next step. |
With triethylamine In dichloromethane at 0 - 20℃; for 13h; | 53.2 10331] Step 2: To a DCM (15 mE) solution of the alcohol(1.29 g, 8.9 mmol) was added triethylamine (1.8 mE, 13.0 mmol). The solution was cooled to 0° C. before methanesulfonyl chloride (0.93 mE, 12.0 mmol) was added dropwise. The resulting mixture was allowed to warm to RT over 13 h. The reaction was diluted with DCM and washed with water, the organic phase separated, dried (Na2 SO4), filtered and the filtrate concentrated in vacuo. No further purification was necessary to afford methyl 3-((methylsulfonyl)oxy)cyclo- pentanecarboxylate. | |
With triethylamine In dichloromethane at 0 - 25℃; for 2h; | 16 Preparation 16 cis/trans-methyl 3-((methylsulfonyl)oxy)cyclopentanecarboxylate In a 25 mL round-bottomed flask, methyl 3-hydroxycyclopentanecarboxylate (0.22 g, 1.5 mmol) was dissolved in 2 mL DCM and cooled to 0° C. Et3N (0.39 g, 0.54 mL, 3.9 mmol) was added followed by a slow addition of MsCl (0.2 g, 0.14 mL, 1.8 mmol). The solution was warmed to 25° C. and stirred for 2 hr. The reaction was quenched with sat. NaHCO3 and extracted with DCM (3*20 mL). The organic layers were combined, washed with brine (2*15 mL), and concentrated in vacuo. 1H NMR (500 MHz, CDCl3-d) δ ppm 5.29-5.23 (m, 0.32H) 5.16 (tt, J=5.9, 4.0 Hz, 1H) 3.70 (s, 3H) 3.68 (s, 1.3H) 3.13-3.02 (m, 0.3H) 3.01 (s, 3H) 2.99 (s, 1.2H) 2.90-2.78 (m, 1H) 2.40-1.85 (m, 8H). 3:1 diastereomer ratio. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | Stage #1: 3-hydroxycyclopentanecarboxylic acid methyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.33333h; Inert atmosphere; Stage #2: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78 - 0℃; for 1.08333h; Inert atmosphere; Stage #3: methyl iodide In tetrahydrofuran at 0 - 20℃; for 2.75h; | 120.1 10529] Step 1: To a nitrogen flushed vessel containing NaR (158mg, 6.59 mmol), THF (6 mE) was added followed by the dropwise addition of methyl 3-hydroxycyclopentanecar- boxylate (950 mg, 6.59 mmol). The resulting suspension was allowed to stir at 0° C. for 35 mm. and then at RT for 45 mm. In a separate round bottom flask flushed with nitrogen, diisopropylamine 1.1 mE, 7.91 mmol) in THF (10 mE) was cooled to -78° C. before n-l3uEi (2.5 M in hexanes, 3.1 mE, 7.91 mmol) was added dropwise over 5 mm. The resulting solution was allowed to stir at -78° C. for 30 mi and then at 0° C. for 30 mm. The EDA thus generated was then added dropwise to the sodium alkoxide suspension at -78° C. Finally, methyl iodide (0.492 mE, 7.91 mmol) was added and stirred at 0° C. for 15 mm and then at RT for 2.5 h. The crude mixture was quenched with sat. NH4C1 solution and extracted in ethet The combined organics were then washed further with brine, dried over Na2504, filtered and the filtrate concentrated in vacuo. Purification by way of column chromatography (5i02, 0-100% EtOAc/hexanes) afforded methyl 3-hydroxy-1 -methylcyclopentanecarboxylate (200 mg, 20% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 13 h / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 2.2: 4.5 h / 50 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 13 h / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 2.2: 4.5 h / 50 °C / Sealed tube 3.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium carbonate / toluene / 13 h / 80 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 13 h / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 2.2: 4.5 h / 50 °C / Sealed tube 3.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium carbonate / toluene / 13 h / 80 °C / Sealed tube 4.1: lithium hydroxide; methanol / tetrahydrofuran / 13 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1.33 h / 0 - 20 °C / Inert atmosphere 1.2: 1.08 h / -78 - 0 °C / Inert atmosphere 1.3: 2.75 h / 0 - 20 °C 2.1: pyridine / dimethyl sulfoxide / 13 h / 20 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 1.33 h / 0 - 20 °C / Inert atmosphere 1.2: 1.08 h / -78 - 0 °C / Inert atmosphere 1.3: 2.75 h / 0 - 20 °C 2.1: pyridine / dimethyl sulfoxide / 13 h / 20 °C / Sealed tube 3.1: caesium carbonate / dimethyl sulfoxide / 16 h / 60 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 1.33 h / 0 - 20 °C / Inert atmosphere 1.2: 1.08 h / -78 - 0 °C / Inert atmosphere 1.3: 2.75 h / 0 - 20 °C 2.1: pyridine / dimethyl sulfoxide / 13 h / 20 °C / Sealed tube 3.1: caesium carbonate / dimethyl sulfoxide / 16 h / 60 °C / Sealed tube 4.1: lithium hydroxide; methanol / 13 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 6 h / 0 - 80 °C 2: sodium tetrahydroborate / tetrahydrofuran / 12 h / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 1 h / 80 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 4 h / 0 - 20 °C 2: N,N-dimethyl-formamide / 16 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 4 h / 0 - 20 °C 2: N,N-dimethyl-formamide / 16 h / 60 °C 3: acetic acid; sodium acetate trihydrate; dihydrogen peroxide / 16 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 4 h / 0 - 20 °C 2: N,N-dimethyl-formamide / 16 h / 60 °C 3: acetic acid; sodium acetate trihydrate; dihydrogen peroxide / 16 h / 60 °C 4: lithium hydroxide monohydrate / water; tetrahydrofuran / 12 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 4 h / 0 - 20 °C 2: N,N-dimethyl-formamide / 16 h / 60 °C 3: acetic acid; sodium acetate trihydrate; dihydrogen peroxide / 16 h / 60 °C 4: 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With 1H-imidazole In tetrahydrofuran at 20℃; for 16h; | 21.2; 22.2; 23.2 Step 2. Synthesis of methyl 3-(tert-butyldimethylsilyloxy)cyclopentanecarboxylate To a solution of methyl 3-hydroxycyclopentanecarboxylate (3.1 g, 21.5 mmol, 1.0 eq)THF (40 mL), TBSC1 (6.5 g, 43 mmol, 2.0 eq) and imidazole (2.9 g, 43 mmol, 2.0 eq) was added. The mixture was stirred at ft for 16 h. The solvent was removed in vacuo. The residuewas purified by silica gel chromatography (PE/EA = 10/1) to give methyl 3-(tert- butyldimethylsilyloxy)cyclopentanecarboxylate (2.3 g, Y: 43%) as light yellow oil. ESI-MS (M+H): 259.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1H-imidazole / tetrahydrofuran / 16 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1H-imidazole / tetrahydrofuran / 16 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1H-imidazole / tetrahydrofuran / 16 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4: titanium(IV) tetraethanolate / tetrahydrofuran / 16 h / 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1H-imidazole / tetrahydrofuran / 16 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4.1: titanium(IV) tetraethanolate / tetrahydrofuran / 16 h / 70 °C / Inert atmosphere 5.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 5.2: 3 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; | 51.C Step C: 3- (hydroxymethyl) cyclopentanol To a solution of 3-hydroxycyclopentanecarboxylic acid ester (558 mg, 4.0 mmol) in dry tetrahydrofuran(10 ml) was added lithium aluminum hydride (308 mg, 8.1 mmol) slowly. The reaction was warmed to room temperature and the reaction was continued for 2 hours. The system was quenched with water and concentrated under reduced pressure to remove the solvent. Ethyl acetate was added to the residue, and the organic phase was washed with water and saturated brine. The organic phase was dried and concentrated and then separated by column chromatography (ethyl acetate / n-hexane = 1: 1) to give the title compound (262 mg, 58%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: triethylamine / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: triethylamine / dichloromethane / 2 h / 20 °C 3: dimethyl sulfoxide / 12 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: triethylamine / dichloromethane / 2 h / 20 °C 3: dimethyl sulfoxide / 12 h / 80 °C 4: trifluoroacetic acid / 2 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; | 1.2 (3 - Methoxycarbonylcyclopentyl) 3 - [(1 R) - 1 - phenylethyl] imidazole - 4 - carboxylate The 3 - [(1 R) -1 - phenyl ethyl] imidazole -4 - carboxylic acid (1 A) (1.0 g, 4.6 mmol) suspended in dichloromethane (20 ml) in, adding 3 - hydroxy cyclopentyl carboxylic acid methyl ester (4 B) (1.0 g, 6.9 mmol), 1 - (3 - dimethylamino propyl) -3 - ethyl carbodiimide hydrochloride (1.3 g, 6.9 mmol) and 4 - dimethylamino pyridine (0.85 g, 6.9 mmol), stirring at room temperature for 2 hours. The reaction solution for sequentially saturated sodium dihydrogen phosphate aqueous solution (30 ml × 2) and saturated salt water (30 ml × 1) washing, drying of the organic phase with anhydrous sodium sulfate, filtered, the filtrate is concentrated under reduced pressure, the residue separation and purification with silica gel column chromatography (ethyl acetate/petroleum ether (v/v)=1/20 - 1/5), to obtain the title compound (3 - methoxy carbonyl cyclopentyl) 3 - [(1 R) -1 - phenyl ethyl] imidazole -4 - carboxylic acid ester (compound 4), colorless oil of, (0.8 g, yield 50%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 25 °C 2.2: 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: Cs2CO3 / N,N-dimethyl-formamide / 13 h / 100 °C |
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