ChemicalBook CAS DataBase List 4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXEN-1-YL]-MORPHOLINE

4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXEN-1-YL]-MORPHOLINE synthesis

4synthesis methods

Product Name:4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXEN-1-YL]-MORPHOLINE
CAS Number:1046793-56-9
Molecular formula:C16H28BNO3
Molecular Weight:293.21

4-morpholinocyclohex-1-enyl trifluoromethanesulfonate

1046793-55-8
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73183-34-3
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4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXEN-1-YL]-MORPHOLINE

1046793-56-9
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Yield: 86%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane for 12 h;Reflux;Inert atmosphere;

Steps:

2 Step 2: 4-(4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)cyclohex-3-enyl)morpholine
[00305] A mixture of 4-morpholinocyclohex-1-enyl trifluoromethanesulfonate (4 g, 12.69 mmol, 1.00 equiv), 4,4,5 ,5-tetramethyl-2- (tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1,3,2- dioxaborolane (3.87 g, 15.24 mmol, 1.20 equiv), potassium acetate (3.73 g, 38.01 mmol, 3.00 equiv) and Pd(dppf)C12 (930 mg, 1.27 mmol, 0.10 equiv) in 1,4-dioxane (100 mL) was refluxed under nitrogen for 12 h. The reaction mixture was cooled to room temperature, filtered and then concentrated under vacuum. The residue was purified on a silica gel column eluted with 50-100% of ethyl acetate in petroleum ether to give 3.2 g (86%) of 4-(4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)cyclohex-3-enyl)morpholine as a yellow oil. ‘H-NMR (300 MHz, CDC13): 6.60-6.55 (m, 1H), 3.80-3.66 (m, 4H), 2.70-2.25 (m, 8H), 2.20-1.90 (m, 4H), 1.25 (s, 12H) ppm.

References:

EPIZYME, INC.;CHESWORTH, Richard;MITCHELL, Lorna, Helen;SHAPIRO, Gideon WO2014/153226, 2014, A1 Location in patent:Paragraph 00305

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References

4746-97-8 Synthesis

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References

4-(1,4-dioxaspiro[4.5]decan-8-yl)morpholine

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1046793-56-9
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References