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CAS No. : | 63674-48-6 | MDL No. : | MFCD05096196 |
Formula : | C13H15NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PMFQUYSCBXNYOR-UHFFFAOYSA-N |
M.W : | 233.26 | Pubchem ID : | 4739040 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 67.79 |
TPSA : | 57.61 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) : | -6.84 cm/s |
Log Po/w (iLOGP) : | 1.6 |
Log Po/w (XLOGP3) : | 1.25 |
Log Po/w (WLOGP) : | 1.36 |
Log Po/w (MLOGP) : | 1.59 |
Log Po/w (SILICOS-IT) : | 1.91 |
Consensus Log Po/w : | 1.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -2.2 |
Solubility : | 1.46 mg/ml ; 0.00627 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.06 |
Solubility : | 2.04 mg/ml ; 0.00875 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.66 |
Solubility : | 0.514 mg/ml ; 0.0022 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.2 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
70% | at 130℃; for 0.75h; | 1.a Example 1: Synthesis of l-(2,6-dimethyIphenyl)-3-isopropyl-5-oxo-pyrrolidine-3- carboxylic acid [3,5-bis(trifluoromethyl)phenyl] amidestep e step d[0072] a) A mixture of 2,6-dimethylaniline (121 g, 1 mol) and itaconic acid (130 g, 1 mol) was heated to 130 °C for 45 min in a flask open to the atmosphere, letting the generated steam vent. The heating source was removed and 0.8 L of ethyl acetate was added under vigorous stirring, while the mixture was still hot (allowing initially for some reflux). The mixture was then let to cool to room temperature while stirring. The solids were filtered off, washed with 0.4 L of ethyl acetate and dried in air to give 164 g (70% yield) of colorless crystals. LC-MS Rt (retention time): 0.54 min, MS: (ES) mlz 234 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine In dichloromethane at 10 - 20℃; for 14h; Cooling with ice; | 31 Example 31: Synthesis of tert-butyl l-(2,6-dimethyIphenyl)-5-oxopyrrolidine-3- carboxylate[0169] a) To a 2 L, 3-neck flask was added l-(2,6-dimethylphenyl)-5-oxopyrrolidine-3- carboxylic acid (93 g, 0.40 mol), anhydrous tert-butanol (60 mL, 0.63 mol), TEA (110 mL, 0.79 mol), DMAP (5.0 g, 41 mmol), and CH2C12 (800 mL). After the mixture was cooled in an ice bath under nitrogen atmosphere with mechanical stirring, 2,4,6-trichlorobenzoyl chloride (108 g, 0.443 mol) was added in portions over the course of 15 minutes such that the temperature did not exceed 10 °C. After the addition was complete, the ice bath was removed, the mixture was allowed to warm to room temperature and stirred for an additional 14 h. TLC and LCMS indicated complete consumption of starting material and formation of desired product. The mixture was filtered and the filter cake was washed with EtOAc (100 mL) and ether (150 mL). The filtrate was washed with two 200 mL portions of 1 MNaHS04, four 200 mL portions of saturated aqueous NaHC03, and brine (100 mL). After drying over MgS04, the organic phase was treated with 24 g of silica gel, and filtered. The filtrate was concentrated to 250 mL and diluted with hexane. A crystalline precipitate began to form, and an initial crop of 66 g was recovered. The filtrate was recovered andrecrystallized (ether/hexanes) to afford a second crop (27 g); overall yield, 93 g (81%). LCMS Rt (retention time): 2.28 min, MS: (ES) m/z 290 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With acetyl chloride at 64℃; for 1h; | 1.b [0073] b) Acetyl chloride (2.40 g, 30.9 mmol) was added dropwise to 400 mL of methanol. l-(2,6-dimethylphenyl)-5-oxo-pyrrolidine-3-carboxylic acid (144 g, 618 mmol, prepared in step a above) was added to the solution followed by trimethyl ortho formate (67 mL, 618 mmol). he mixture was heated to 64 °C for 1 h and then concentrated in vacuo to give 152 g (99% yield) of pure product as an oil. LC-MS Rt (retention time): 1.49 min, MS: (ES) mlz 248 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: dmap; triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 14 h / 10 - 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / 0 - 20 °C 3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / <i>tert</i>-butyl alcohol; tetrahydrofuran / 18 h / 20 °C 4.1: sodium periodate / water; tetrahydrofuran / 20 °C 5.1: ammonium acetate; acetic acid / tetrahydrofuran; methanol / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: dmap; triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 14 h / 10 - 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / 0 - 20 °C 3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / <i>tert</i>-butyl alcohol; tetrahydrofuran / 18 h / 20 °C 4.1: sodium periodate / water; tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dmap; triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 14 h / 10 - 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / 0 - 20 °C 3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / <i>tert</i>-butyl alcohol; tetrahydrofuran / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: dmap; triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 14 h / 10 - 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -50 - 20 °C 3.2: 2 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.17 h / 20 °C 3.2: 2 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 80 °C / sealed vial 3.2: 0.25 h / 20 °C 4.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / acetonitrile / 16 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 3.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.17 h / 20 °C 3.2: 0.5 h / 100 °C / a sealed vial |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 80 °C / sealed vial 3.2: 0.25 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 2.2: 2 h / -50 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 70 °C 3.2: 0 °C 4.1: brucine / isopropyl alcohol / 75 °C 5.1: methanol / 0.17 h / 20 °C 6.1: hydrogen / palladium 10% on activated carbon / methanol / 20 °C 7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 7.2: 2 h / -50 - 20 °C 8.1: n-butyllithium / tetrahydrofuran / 0.17 h / 20 °C 8.2: 75 °C / A sealed vial |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 2.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 2.2: 2 h / -50 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 70 °C 3.2: 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 2.2: 2 h / -50 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 70 °C 3.2: 0 °C 4.1: brucine / isopropyl alcohol / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 2.2: 2 h / -50 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 70 °C 3.2: 0 °C 4.1: brucine / isopropyl alcohol / 75 °C 5.1: methanol / 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 2.2: 2 h / -50 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 70 °C 3.2: 0 °C 4.1: brucine / isopropyl alcohol / 75 °C 5.1: methanol / 0.17 h / 20 °C 6.1: hydrogen / palladium 10% on activated carbon / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 2.2: 2 h / -50 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 70 °C 3.2: 0 °C 4.1: brucine / isopropyl alcohol / 75 °C 5.1: methanol / 0.17 h / 20 °C 6.1: hydrogen / palladium 10% on activated carbon / methanol / 20 °C 7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 7.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 2.2: 1 h / -50 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C 3.2: 0 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 4.2: 2 h / -50 - 20 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 2 h / 20 °C 6.1: 1H-imidazole; triphenylphosphine; iodine / toluene / 1 h / 100 °C 7.1: acetonitrile / 80 °C 8.1: n-butyllithium / tetrahydrofuran / 0.17 h / 20 °C 8.2: 2 h / 70 °C / A sealed vial |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 2.2: 1 h / -50 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C 3.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 2.2: 1 h / -50 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C 3.2: 0 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 4.2: 2 h / -50 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 2.2: 1 h / -50 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C 3.2: 0 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 4.2: 2 h / -50 - 20 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 2.2: 1 h / -50 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C 3.2: 0 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 4.2: 2 h / -50 - 20 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 2 h / 20 °C 6.1: 1H-imidazole; triphenylphosphine; iodine / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 2.2: 1 h / -50 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C 3.2: 0 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -50 °C 4.2: 2 h / -50 - 20 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 2 h / 20 °C 6.1: 1H-imidazole; triphenylphosphine; iodine / toluene / 1 h / 100 °C 7.1: acetonitrile / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.33 h / -78 °C 2.2: 16 h / -78 - 20 °C 3.1: sodium hydroxide; water / ethanol / 2 h / 80 °C 4.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 16 h / 0 - 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.08 h / -78 °C 5.2: 14 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.33 h / -78 °C 2.2: 16 h / -78 - 20 °C 3.1: sodium hydroxide; water / ethanol / 2 h / 80 °C 4.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.33 h / -78 °C 2.2: 16 h / -78 - 20 °C 3.1: sodium hydroxide; water / ethanol / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.33 h / -78 °C 2.2: 16 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.08 h 3.2: 10 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C 3.2: 1 h / -78 - 20 °C 4.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h 4.2: 2 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C 3.2: 1 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C 3.2: 1 h / -78 - 20 °C 4.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h 4.2: 2 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C 3.2: 1 h / -78 - 20 °C 4.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h 4.2: 2 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C 3.2: 1 h / -78 - 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.08 h 4.2: 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: sodium hydroxide; water / ethanol / 1.75 h 4.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.58 h / 0 - 20 °C 4.2: 55 °C 5.1: sulfuric acid / 1,4-dioxane / 110 °C 6.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.25 h / 0 - 20 °C 6.2: 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: sodium hydroxide; water / ethanol / 1.75 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: sodium hydroxide; water / ethanol / 1.75 h 4.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.58 h / 0 - 20 °C 4.2: 55 °C 5.1: sulfuric acid / 1,4-dioxane / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / -50 - 20 °C 3.1: sodium hydroxide; water / ethanol / 1.75 h 4.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.58 h / 0 - 20 °C 4.2: 55 °C 5.1: sulfuric acid / 1,4-dioxane / 110 °C 6.1: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 80 °C / sealed vial 3.2: 0.25 h / 20 °C 4.1: brucine / ipa / 80 °C / Resolution of racemate 5.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0 - 20 °C 5.2: 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 80 °C / sealed vial 3.2: 0.25 h / 20 °C 4.1: brucine / ipa / 80 °C / Resolution of racemate 5.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0 - 20 °C 5.2: 55 °C 5.3: 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol / 1 h / 80 °C / sealed vial 3.2: 0.25 h / 20 °C 4.1: brucine / ipa / 80 °C / Resolution of racemate 5.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0 - 20 °C 5.2: 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C 2.2: 1 h / -78 - 20 °C 3.1: Burgess Reagent / tetrahydrofuran / 1 h / 75 °C 4.1: water; lithium hydroxide / methanol / 1 h / 75 °C 4.2: pH 4 5.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.08 h / 20 °C 5.2: 18 h / 75 °C 6.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: acetyl chloride / 1 h / 64 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 2.2: 1 h / -50 - 20 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 18 h / 0 - 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 20 °C 6.1: Burgess Reagent / tetrahydrofuran / 2 h / 75 °C 7.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 7.2: 2 h / 75 °C 8.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; methanol / 24 h / 20 °C |
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