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[ CAS No. 912444-89-4 ]

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Chemical Structure| 912444-89-4
Chemical Structure| 912444-89-4
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Product Details of [ 912444-89-4 ]

CAS No. :912444-89-4 MDL No. :MFCD11114566
Formula : C14H23NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :269.34 g/mol Pubchem ID :25194565
Synonyms :

Safety of [ 912444-89-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 912444-89-4 ]

  • Upstream synthesis route of [ 912444-89-4 ]
  • Downstream synthetic route of [ 912444-89-4 ]

[ 912444-89-4 ] Synthesis Path-Upstream   1~5

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  • [ 912444-88-3 ]
  • [ 912444-89-4 ]
YieldReaction ConditionsOperation in experiment
95% With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 60℃; for 1 h; EXAMPLE 42D; 1-tert-butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate A solution of example 42C (0.77 g, 2.1 mmol) in 30 mL of benzene was treated with DBU (0.9 ml ) at 60° C. for 1 hour. After cooling, the reaction mixture was concentrated and the residue was purified by flash column chromatography (30percent EtOAc in hexane) to give the title product (540 mg, 95percent yield). MS (DCI/NH3) m/z 270 (M+H)+.
3.31 g With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 60℃; A solution of 1-(tert-butyl) 4-ethyl 5-((methylsulfonyl)oxy)azepane-1,4-dicarboxylate (5.0 g, 13.7 mmol)and DBU (10 mL) in toluene (50 mL) was heated to 60° C.and stirred overnight. Upon completion of the reaction, thereaction mixture was quenched with water (70 mL) andextracted with EtOAc (100 mLx3). The combined organicphase was dried over Na2S04 and concentrated underreduced pressure. The residue was purified by silica-gelcolunm chromatography to afford 3.31 g of 1-(tert-butyl)4-ethyl 2,3,6,7 -tetrahydro-1H-azepine-1 ,4-dicarboxylate asa yellow oil. LC-MS (ESI+ ): m/z 292 [M+Nat.
56.8 g With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran To a solution of 1-tert-butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate (13) (94.5 g, 0.331 mol) in MeOH (1.3 L), NaBH4 (3.74 g, 0,099 mol) was added portionwise at 0 °C and the mixture was stirred at the same temperature for additional 1 h. The resulting solution was concentrated under vacuum. The residue was diluted with H2O (700 mL) and extracted with EtOAc (3300 mL). The combined organic extracts were washed with H2O (200 mL), brine (200 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to give 80.1 g of crude product, that was used in the next step without further purification. To a solution of the crude 1-tert-butyl 4-ethyl 5-hydroxyazepane-1,4-dicarboxylate (80.1 g) in CH2Cl2 (1.1 L), NEt3 (117 mL, 0.834 mol) was added at 0 °C. Methanesulfonyl chloride (36.5 mL, 0.474 mol) was added dropwise while the temperature was maintained below 5 °C and the solution was stirred at rt for 4 h. The resulting mixture was treated with 10percent aq NaHCO3 (500 mL), organic phase was separated, and the aqueous phase was extracted with CH2Cl2 (3300 mL). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give 95.3 g of crude product, which was used in the next step without further purification. S4 To a solution of obtained crude 1-tert-butyl 4-ethyl 5-((methylsulfonyl)oxy)azepane-1,4-dicarboxylate (95.3 g) in THF (2.1 L), DBU (54.6 mL, 0.365 mol) was added in one portion and the reaction mixture was stirred overnight. The resulting solution was diluted with EtOAc (500 mL), washed with brine (4500 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to give the title product. Yield: 56.8 g (64 percent); colorless oil. The compound existed as ca. 1:1 mixture of rotamers.
Reference: [1] Patent: US2006/229289, 2006, A1, . Location in patent: Page/Page column 22
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 23, p. 6072 - 6075[3] Angew. Chem., 2013, vol. 125, # 23, p. 6188 - 6191
[4] Patent: US2018/258065, 2018, A1, . Location in patent: Paragraph 0149
[5] Tetrahedron Letters, 2018, vol. 59, # 52, p. 4611 - 4615
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YieldReaction ConditionsOperation in experiment
66% With methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 2 h; Example 18C
1-tert-butyl 4-ethyl 2,3,6,7-tetrahydro-1H-azepine-1,4-dicarboxylate
To a solution of EXAMPLE 18B (21 g, 73 mmol), DBU (22 g, 146 mmol) in toluene (200 mL) was added dropwise MsCl (14.56 g, 128 mmol).
After the dropwise addition was completed, the mixture was stirred at 110° C. for 2 h, and cooled to room temperature, and then water (200 mL) was added to quench.
The aqueous layer was extracted with EtOAc (200 mL*2).
The combined organic layers were washed with water, brine, dried over Na2SO4, filtered and evaporated.
The residue was purified by column chromatograph on silica gel to provide the title compound (13 g, yield: 66percent). LCMS (ESI) m/z: 270 (M+1).
Reference: [1] Patent: US2017/29430, 2017, A1, . Location in patent: Paragraph 0322
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 23, p. 6072 - 6075[3] Angew. Chem., 2013, vol. 125, # 23, p. 6188 - 6191
[4] Patent: US2018/258065, 2018, A1,
[5] Tetrahedron Letters, 2018, vol. 59, # 52, p. 4611 - 4615
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  • [ 141642-82-2 ]
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 23, p. 6072 - 6075[2] Angew. Chem., 2013, vol. 125, # 23, p. 6188 - 6191
[3] Patent: US2017/29430, 2017, A1,
[4] Patent: US2018/258065, 2018, A1,
[5] Tetrahedron Letters, 2018, vol. 59, # 52, p. 4611 - 4615
  • 4
  • [ 79099-07-3 ]
  • [ 912444-89-4 ]
Reference: [1] Patent: US2018/258065, 2018, A1,
[2] Tetrahedron Letters, 2018, vol. 59, # 52, p. 4611 - 4615
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YieldReaction ConditionsOperation in experiment
55% With hydrogen In methanol EXAMPLE 42E; 1-tert-butyl 4-ethyl azepane-1,4-dicarboxylate A solution of example 42D (0.54 g, 2.0 mmol) in 20 ml of MeOH was treated with 10percent Pd/C (50 mg) under hydrogen overnight. Solid material was filtered off and the filtrate was concentrated. The residue was purified by flash column chromatography (20percent EtOAc in hexane) to give the title product (310 mg, 55percent yield). MS (DCI/NH3) m/z 272 (M+H)+.
Reference: [1] Patent: US2006/229289, 2006, A1, . Location in patent: Page/Page column 22-23
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