tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate
• CAS No.: 1200575-36-5
• Molecular Formula: C₂₅H₃₂N₂O₅S
• Molecular Weight: 472.605
• Mol file: 1200575-36-5.mol

Synonyms:tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate

Chemical Property of tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate

There total 9 articles about tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 13.0%

tert-butyl 4-(7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-yl)piperidine-1-carboxylate (1200576-15-3) + 4-methanesulphonylphenylboronic acid (149104-88-1) → tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate (1200575-36-5)

Guidance literature:

With sodium hydrogencarbonate; triphenylphosphine; palladium diacetate; In ethanol; at 80 ℃;

Reference yield:

6-amino-2-methylbenzoxazole (5676-60-8) → tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate (1200575-36-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water; hydrogen bromide; sodium nitrite / 0.17 h / 0 °C

1.2: 0 °C

2.1: hydrogenchloride; water / ethanol / 3 h / 100 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h

3.2: 20 °C

4.1: sodium tetrahydroborate / ethanol / 6 h

5.1: sodium hydrogencarbonate; triphenylphosphine / palladium diacetate / ethanol / 80 °C

With hydrogenchloride; sodium tetrahydroborate; water; hydrogen bromide; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine; sodium nitrite; palladium diacetate; In ethanol; N,N-dimethyl-formamide;

Reference yield:

2-methyl-6-nitrobenzoxazole (5683-43-2) → tert-butyl 4-{7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-piperidine-1-carboxylate (1200575-36-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: iron; ammonium chloride / methanol; water / 2 h / 70 °C

2.1: water; hydrogen bromide; sodium nitrite / 0.17 h / 0 °C

2.2: 0 °C

3.1: hydrogenchloride; water / ethanol / 3 h / 100 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h

4.2: 20 °C

5.1: sodium tetrahydroborate / ethanol / 6 h

6.1: sodium hydrogencarbonate; triphenylphosphine / palladium diacetate / ethanol / 80 °C

With hydrogenchloride; sodium tetrahydroborate; water; hydrogen bromide; iron; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; triphenylphosphine; sodium nitrite; palladium diacetate; In methanol; ethanol; water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl 4-(7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-yl)piperidine-1-carboxylate

4-methanesulphonylphenylboronic acid

6-amino-2-methylbenzoxazole

2-methyl-6-nitrobenzoxazole

Downstream raw materials:

7-[4-(methylsulfonyl)phenyl]-3-piperidin-4-yl-3,4-dihydro-2H-1,4-benzoxazine.

3-[1-(cyclohexylacetyl)piperidin-4-yl]-7-[4-(methylsulfonyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazine trifluoroacetate