| 94% |
With triethylsilane; indium(III) bromide In chloroform at 60℃; for 20h; Inert atmosphere; |
|
| 92% |
With bis(trimethylsilyl)amide yttrium(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 100℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; |
|
| 92% |
With bis(trimethylsilyl)amide yttrium(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 80℃; for 24h; Inert atmosphere; |
4 The synthesis of 4-benzylmorpholine has the following chemical structure
Under the protection of nitrogen, add the raw materials morpholine phenyl ketone (0.5 mmol), pinacol borane (1.2 mmol) and catalyst Y[N(SiMe3)2]3 (10 mol%) in toluene (3 ml) At 80 °C for 24 h, the product separation yield was 92%. |
| 92% |
With phenylsilane-d3; C36H48F6N6NiO5S2 In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique; |
|
| 87% |
Stage #1: 4-benzoylmorpholine With 1,1,3,3-Tetramethyldisiloxane; [((CH3)5C5)IrCl((CH3)2NC6H3C5H4N)]; trityl tetrakis(pentafluorophenyl)borate In 1,1,2,2-tetrachloroethane at 100℃; for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: With hydrogenchloride In diethyl ether; water for 0.166667h; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction; |
|
| 85% |
With phenylsilane; [(k2-P,N)Mn(N(SiMe3)2)] In benzene-d6 at 75℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; |
|
| 84% |
With Triethoxysilane; zinc diacetate In tetrahydrofuran at 20℃; Inert atmosphere; chemoselective reaction; |
|
| 84% |
With Dimethylphenylsilane In toluene at 110℃; for 4h; Inert atmosphere; |
|
| 84% |
With borane-ammonia complex; boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 24h; |
|
| 81% |
With Dimethylphenylsilane In ethyl acetate at 20 - 80℃; for 13h; Green chemistry; |
|
| 80% |
With triiron dodecarbonyl In dibutyl ether at 100℃; for 24h; Inert atmosphere; |
|
| 80% |
Stage #1: 4-benzoylmorpholine With trifluoromethylsulfonic anhydride In dichloromethane at 0 - 5℃; for 0.5h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; dichloromethane at 20℃; |
|
| 80% |
With H2SiEt2 In benzene at 70℃; |
|
| 78% |
With phenylsilane; C36H61FeN2PSi2 In benzene at 80℃; for 23h; Inert atmosphere; Sealed tube; |
|
| 76% |
With titanium tetrachloride; magnesium In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
|
| 76% |
With phenylsilane; caesium carbonate at 80℃; for 24h; Schlenk technique; |
|
| 75% |
With phenylsilane; potassium hydroxide In neat (no solvent) at 20℃; for 4h; |
|
| 74% |
With diethoxymethylane; zinc diacetate In tetrahydrofuran at 65℃; Inert atmosphere; chemoselective reaction; |
|
| 65% |
Stage #1: 4-benzoylmorpholine With dicobalt octacarbonyl In toluene at 100℃; for 3h; Schlenk technique; Inert atmosphere;
Stage #2: With sodium hydroxide In methanol; water; toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; chemoselective reaction; |
|
| 52% |
With sulfuric acid; N,N,N,N',N',N'-hexamethyl-1,3-propanediammonium methylsulfate In methanol at 45℃; Electrolysis; |
|
| 89 %Chromat. |
With tris(pentafluorophenyl)borate In toluene at 100℃; for 18h; Sealed tube; |
|
| > 99 %Spectr. |
With phenylsilane; (bis[(2-diphenylphosphino)phenyl]ether)CoCl2; lithium triethylborohydride In tetrahydrofuran; benzene-d6 at 60℃; for 5h; Inert atmosphere; Sealed tube; |
|
|
With phenylsilane; zinc diacetate; benzoic acid In toluene at 110℃; for 2h; |
|
| 90 %Spectr. |
With 1,3-diphenyl-disiloxane; zinc diacetate In water; ethyl acetate at 23℃; for 24.5h; Inert atmosphere; |
Reduction of Tertiary Amides; General Procedure
General procedure: To a tared 2-dram vial were added EtOAc (0.500 mL, 0.500 M), DPDS(115 mg, 0.500 mmol, 2.00 equiv), and zinc acetate (4.60 mg, 0.025mmol, 10.0 mol%). The vial was capped and the contents stirred at550 rpm for 30 minutes. After this time, the corresponding tertiaryamide (0.250 mmol, 1.00 equiv) was added and the resulting mixturewas stirred at 23 °C for 24 hours. The reaction mixture was blown dry(nitrogen gas), and Qnmr was performed using hexamethylbenzeneas an internal standard. For isolation, the reaction mixture was dilutedwith EtOAc (3.5 mL) and 2 M NaOH (3 mL). This mixture was left tostir for 1 hour before extraction with EtOAc (3 × 4 mL). The combinedorganics were dried over MgSO4 and concentrated under reducedpressure. Purification by flash chromatography afforded the targetamine. Purification by flash chromatography was performed to confirm conversion,but resulted in loss of product, hence, calculated yields (determinedby 1H NMR analysis using hexamethylbenzene as an internalstandard) and not isolated yields are reported below. In certaincases, siloxane impurities co-eluted with the amine of interest as a resultof their polar nature and are observed as impurities in the aromaticregion of the NMR spectra. |
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