No renderable structure data available
CNS(=O)(=O)C1CC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-methylcyclopropanesulfonamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 180891-39-8 |
| Database ID | 15334537 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-methylcyclopropanesulfonamide (CAS 180891-39-8) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 15334537
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1bc700dea1494c7cb04f180d687cf86eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6f666486faf8405caa80dba07fd1ea67Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-60d677cdf7fa4f07880cdfea7e7adb0aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-01e80869be5c461c9039f9f56bb1b484Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)piperidin-2-one (Example 414, Step B) and N-methylcyclopropanesulfonamide by a procedure similar to the one described in Example 201, Step A. The product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g), eluting with a gradient of 0% to 80% EtOAc in hexane, to provide the title compound as an oil. Mass Spectrum (ESI) m/z=665.2 (M+1). The product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g) eluting with a gradient of 0% to 80% EtOAc in hexane
Source ID: ord-3473922d6b974e70a42997fc9c59ec44Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methoxypiperidin-2-one (124 mg, 0.268 mmol; Example 203, Step D) in toluene (1.3 mL) was added N-methylcyclopropanesulfonamide (109 mg, 0.804 mmol). The mixture was evacuated and backfilled with argon (5×). Cyanomethylenetributylphosphorane (0.211 mL, 0.804 mmol) was added. The mixture was evacuated and backfilled with argon (5×). The mixture was heated in a 70° C. oil bath for 12 hours then cooled to room temperature and stirred for 2 days at room temperature. The mixture was loaded onto silica gel and the product was eluted with 20-60% ethyl acetate/hexanes. The residue was one more time purified by flash chromatography on silica gel (12 g column, eluent: 10 to 60% ethylacetate/hexanes) to afford the title compound. The mixture was evacuated The mixture was evacuated then cooled to room temperature the product was eluted with 20-60% ethyl acetate/hexanes purified by flash chromatography on silica gel (12 g column, eluent: 10 to 60% ethylacetate/hexanes)
Source ID: ord-659fe68aae894de5b9ef12b22395c98aConditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-ethyl-1-((S)-1-hydroxybutan-2-yl)piperidin-2-one (147 mg, 0.319 mmol; Example 202, Step B) and N-methylcyclopropanesulfonamide (129 mg, 0.958 mmol) were dissolved in toluene (2 mL). The mixture was evacuated and backfilled with argon (5×). Cyanomethylenetributylphosphorane (0.251 mL, 0.958 mmol) was added. The mixture was evacuated and backfilled with argon (5 X). The mixture was heated at 70° C. for 2 hours. The mixture was loaded onto silica gel and the product was eluted with 5 to 75% ethyl acetate/hexanes to afford the title compound. The mixture was evacuated The mixture was evacuated the product was eluted with 5 to 75% ethyl acetate/hexanes
Source ID: ord-b7f6cd354edb41d88fd7dfd727d36972Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A flask, containing a solution of methyl 2-((3S,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-2-oxopiperidin-3-yl)propanoate (195 mg, 0.408 mmol; Example 127, Step E) and N-methylcyclopropanesulfonamide (165 mg, 1.223 mmol) in toluene (2038 μL) was evacuated and backfilled with Ar (5×). Then cyanomethylenetributylphosphorane (321 μL, 1.223 mmol) was added. The light brownish orange mixture was heated to 70° C. for 2 h. More N-methylcyclopropanesulfonamide (134 mg, 0.991 mmol) was added and the mixture was heated to 70° C. for 2 h. The mixture was heated to reflux overnight and then cooled to room temperature. The mixture was diluted with EtOAc and sat. aq. NaCl solution. The layers were separated. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (4 g column eluent: 0 to 100% EtOAc in hexanes) to give the title compound. was evacuated the mixture was heated to 70° C. for 2 h The mixture was heated to reflux overnight cooled to room temperature The layers were separated The organic layer was dried over Na2SO4 concentrated under reduced pressure The residue was purified by flash chromatography on silica gel (4 g column eluent: 0 to 100% EtOAc in hexanes)
Source ID: ord-1b2ddaa955a94d03bb2fef5b80d58975Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)piperidin-2-one (Example 414, Step B) and N-methylcyclopropanesulfonamide by a procedure similar to the one described in Example 201, Step A. The product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g), eluting with a gradient of 0% to 80% EtOAc in hexane, to provide the title compound as an oil. The product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g) eluting with a gradient of 0% to 80% EtOAc in hexane
Source ID: ord-1765ce5152f94a0e8465b2cbd230f26cConditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methoxypiperidin-2-one (124 mg, 0.268 mmol; Example 203, Step D) in toluene (1.3 mL) was added N-methylcyclopropanesulfonamide (109 mg, 0.804 mmol). The mixture was evacuated and backfilled with argon (5×). Cyanomethylenetributylphosphorane (0.211 mL, 0.804 mmol) was added. The mixture was evacuated and backfilled with argon (5×). The mixture was heated in a 70° C. oil bath for 12 hours then cooled to room temperature and stirred for 2 days at room temperature. The mixture was loaded onto silica gel and the product was eluted with 20-60% ethyl acetate/hexanes. The residue was one more time purified by flash chromatography on silica gel (12 g column, eluent: 10 to 60% ethylacetate/hexanes) to afford the title compound. The mixture was evacuated The mixture was evacuated then cooled to room temperature the product was eluted with 20-60% ethyl acetate/hexanes purified by flash chromatography on silica gel (12 g column, eluent: 10 to 60% ethylacetate/hexanes)
Source ID: ord-c8da01da06a948e6a4d2c7fd361e5e97Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (3R,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methoxypiperidin-2-one (124 mg, 0.268 mmol; Example 203, Step D) in toluene (1.3 mL) was added N-methylcyclopropanesulfonamide (109 mg, 0.804 mmol). The mixture was evacuated and backfilled with argon (5×). Cyanomethylenetributylphosphorane (0.211 mL, 0.804 mmol) was added. The mixture was evacuated and backfilled with argon (5×). The mixture was heated in a 70° C. oil bath for 12 hours then cooled to room temperature and stirred for 2 days at room temperature. The mixture was loaded onto silica gel and the product was eluted with 20-60% ethyl acetate/hexanes. The residue was one more time purified by flash chromatography on silica gel (12 g column, eluent: 10 to 60% ethylacetate/hexanes) to afford the title compound. The mixture was evacuated The mixture was evacuated then cooled to room temperature the product was eluted with 20-60% ethyl acetate/hexanes purified by flash chromatography on silica gel (12 g column, eluent: 10 to 60% ethylacetate/hexanes)
Source ID: ord-c8da01da06a948e6a4d2c7fd361e5e97Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-ethyl-1-((S)-1-hydroxybutan-2-yl)piperidin-2-one (147 mg, 0.319 mmol; Example 202, Step B) and N-methylcyclopropanesulfonamide (129 mg, 0.958 mmol) were dissolved in toluene (2 mL). The mixture was evacuated and backfilled with argon (5×). Cyanomethylenetributylphosphorane (0.251 mL, 0.958 mmol) was added. The mixture was evacuated and backfilled with argon (5×). The mixture was heated at 70° C. for 2 hours. The mixture was loaded onto silica gel and the product was eluted with 5 to 75% ethyl acetate/hexanes to afford the title compound. The mixture was evacuated The mixture was evacuated the product was eluted with 5 to 75% ethyl acetate/hexanes
Source ID: ord-e4040139c8ab47128082f8b71a47f62cPubChem References
These sources are listed in the compound's public database record.
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