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Structure of 42185-27-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 42185-27-3 |
| Formula : | C8H11NO |
| M.W : | 137.18 |
| SMILES Code : | N#CCC1C(CCCC1)=O |
| MDL No. : | MFCD18431742 |
| InChI Key : | NDKUZEVDMZDUGK-UHFFFAOYSA-N |
| Pubchem ID : | 543553 |
| GHS Pictogram: |
|
| Signal Word: | Danger |
| Hazard Statements: | H301-H311-H331 |
| Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 |
| Class: | 6.1 |
| UN#: | 2810 |
| Packing Group: | Ⅲ |
* 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 |
|---|---|---|
| 34% | General procedure: Following the procedures of Stork,15 the cycloketone and pyrrolidine (1.1equiv) were dissolved in benzene or toluene (300mLmol-1 ketone; toluene for n>1) and refluxed for 5-10h (cyclopentanone and -hexanone) or 24-48h (cycloheptanone and -octanone). Excess pyrrolidine and solvent were removed under reduced pressure and the yellow to brown oily residue was directly used for further reactions. For medium-sized rings a small amount of p-toluenesulfonic acid was added (n>1). (0024) Next, the enamine (typically 5-20g) was dissolved in anhydrous dioxane (400mLmol-1) under an argon atmosphere. Then the electrophile (1.5equiv; chloroacetonitrile for compounds 1, 3, 5 and 7, or acrylonitrile for compounds 2, 4, 6 and 8) was added in one shot using a syringe. Occasionally, more electrophile was added in case of stagnant reactions. The mixture was refluxed for 10-48h until complete conversion of the enamine could be detected by GC-MS. Subsequently, water (200mLmol-1) was added and the biphasic mixture was heated to reflux for 30-60min. Dioxane was then removed by rotary evaporation and the residue was partitioned between EtOAc (2mLmmol-1) and 2N HCl (0.5mLmmol-1). The aqueous phase was extracted with EtOAc (4× same volume as before) and the pooled extracts were dried over sodium sulfate and concentrated under reduced pressure. Purification of the brown crude oils was performed on MPLC or via distillation. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| EXAMPLE 149 2-oxocyclohexaneacetonitrile STR151 Cyclohexanone is reacted with bromoacetonitrile by the method of Example 65 to generate the title compound. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; | EXAMPLE 150 2-(hydroxyimino)cyclohexaneacetonitrile STR152 The product of Example 149 is reacted with hydroxylamine hydrochloride and sodium acetate in ethanol/water by the method of Example 1 to generate the title compound. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | With hydrogen; | EXAMPLE IV In the manner described in Example III, a mixture of 2-oxocyclohexaneacetonitrile and hydrogen is passed over a catalyst composed of rhodium on γ-aluminumoxide (0.5 wt. % Rh). The conversion of the oxonitrile is 99%, and the yields are indole 9%, tetrahydroindole 26% and hexahydroindole 5%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With hydrogen; | EXAMPLE III In the manner described in Example I, but differing in that the temperature of the catalyst and the inert material is kept at 240 C., a mixture of 2-oxocyclohexaneacetonitrile and hydrogen is passed over a catalyst composed of platinum on γ-aluminumoxide (0.5 wt. % Pt). The oxonitrile conversion is 100%, and the yields are indole 18%, tetrahydroindole 19% and hexahydroindole 1%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 69% | With hydrogen; | EXAMPLE II In the manner described in Example 1, a mixture of 2-oxocyclohexaneacetonitrile and hydrogen is passed over a catalyst composed of platinum and γ-aluminumoxide (0.5 wt. % platinum). The oxonitrile conversion is 69%, and the yields are indole 11%, tetrahydroindole 12% and hexahydroindole 1%. |
[ 42185-27-3 ]





| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With cyclopentanone MO-type from Comamonas sp. NCIMB 9872; oxygen; In 1,4-dioxane; for 8h;Enzymatic reaction; | General procedure: LB growth medium was inoculated, induced, and charged with additives as described in Section 4.12. The substrate was then added directly to the shake flask as approx. 10% (w/v) solution in dioxane. Incubation at the appropriate temperature was carried out until the desired degree of conversion was determined via GC control. The aqueous solution was then centrifuged (17kRCF, 15min, 4C) and the supernatant was extracted with EtOAc (5× equal volume). The pooled organic layers were washed with brine, dried over sodium sulfate and concentrated. The crude compounds were purified by chromatography on silica using LP/EtOAc mixtures. |
[ 42185-27-3 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 19%; 34% | With cyclohexanone MO-type from Brachymonas petroleovorans; oxygen; In 1,4-dioxane; for 10.5h;Enzymatic reaction; | General procedure: LB growth medium was inoculated, induced, and charged with additives as described in Section 4.12. The substrate was then added directly to the shake flask as approx. 10% (w/v) solution in dioxane. Incubation at the appropriate temperature was carried out until the desired degree of conversion was determined via GC control. The aqueous solution was then centrifuged (17kRCF, 15min, 4C) and the supernatant was extracted with EtOAc (5× equal volume). The pooled organic layers were washed with brine, dried over sodium sulfate and concentrated. The crude compounds were purified by chromatography on silica using LP/EtOAc mixtures. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 83% | at 285℃; for 1h; | General procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is substantially completed. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic resonance and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10, A-11 and A-12 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99%).In these nitrile product preparation examples, 10 g of phosphorus pentaoxide is preferably added to the reaction vessel as a catalyst at one stage, optionally at the beginning of the reaction. |
[ 42185-27-3 ]
[ 42185-27-3 ]

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