Alternatived Products of [ 1450759-47-3 ]
Product Details of [ 1450759-47-3 ]
CAS No. : | 1450759-47-3 |
MDL No. : | MFCD30491832 |
Formula : |
C20H28ClNO4S
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
413.96
|
Pubchem ID : | - |
Synonyms : |
|
Safety of [ 1450759-47-3 ]
Application In Synthesis of [ 1450759-47-3 ]
* 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.
- Upstream synthesis route of [ 1450759-47-3 ]
- Downstream synthetic route of [ 1450759-47-3 ]
- 1
-
[ 1450759-47-3 ]
-
[ 608141-42-0 ]
Yield | Reaction Conditions | Operation in experiment |
94% |
With 5%-palladium/activated carbon; hydrogen; In methanol; at 20℃;Large scale; |
Finally, the N-benzylated aminosulfone derivative Compound D (100 g, 0.211 mol) was hydrogenated with 5% Pd/C (5.0 g), in methanol solvent (1000 ml) and at room temperature, to afford the pure S-aminosulfone Compound B (49-54 g) with 86-94% yield and >99% chiral and chemical purity. |
- 2
-
[ 60758-86-3 ]
-
[ 1450759-47-3 ]
- 3
-
[ 2627-86-3 ]
-
[ 1450657-28-9 ]
-
[ 1450759-47-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: (<i>S</i>)-1-phenyl-ethylamine; 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one With toluene-4-sulfonic acid In toluene Dean-Stark; Large scale;
Stage #2: With hydrogenchloride; sodium tetrahydroborate; acetic acid Large scale;
Stage #3: With hydrogenchloride In isopropyl alcohol Large scale; |
1
In the second step, upon treatment of the keto derivative (100 g, 0.367 mol) Compound C with (S)-(-)-1-Phenylethylamine (150 ml, 1.165 mol, 3.17 eq) in toluene (500 ml) as solvent with catalytic para-toluenesulfonic acid (14.0 g, 0.073 mol, 0.2 eq) and removal of water by Dean-Stark distillation, an intermediate imine was formed, which was treated, without isolation, with sodium borohydride (20.8 g, 0.551 mol, 1.5 eq) in acidic medium followed by hydrolysis of the resulting borate with aqueous sodium hydroxide or hydrochloric acid, to afford the chiral N-benzylated derivative of aminosulfone, [1-(3-Ethoxy-4-methoxyphenyl)-2-methanesulfonyl ethyl]-(1-phenylethyl)amine (Compound D). This product was isolated as the isopropanol solvate of its hydrochloride salt to afford pure product (137-141 g) in 79-81% yield over two steps, with >99% chemical purity and >99% chiral purity. Enamine formation can also be accomplished using the strong Lewis acid Ti(OEt)4 in tetrahydrofuran as solvent. |