tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate
• CAS No.: 319451-52-0
• Molecular Formula: C₁₈H₂₈N₂O₅Si
• Molecular Weight: 380.516
• Mol file: 319451-52-0.mol

Synonyms:tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate

Chemical Property of tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate

There total 3 articles about tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-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: 46.0%

tert-butyl 3-(4-nitrophenoxy)azetidine-1-carboxylate (319451-51-9) + (trimethylsilyl)methylmagnesium chloride (13170-43-9) → tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate (319451-52-0)

Guidance literature:

tert-butyl 3-(4-nitrophenoxy)azetidine-1-carboxylate; (trimethylsilyl)methylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -5 ℃; for 1h;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3.5h;

DOI:10.1248/cpb.54.163

Reference yield:

4-Fluoronitrobenzene (350-46-9,178603-76-4) → tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate (319451-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / N,N-dimethyl-acetamide / 0.25 h / 20 °C

1.2: 95 percent / N,N-dimethyl-acetamide / 4 h / 20 °C

2.1: tetrahydrofuran; diethyl ether / 1 h / -5 °C

2.2: 46 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / tetrahydrofuran; diethyl ether / 3.5 h / 0 °C

With sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl acetamide;

DOI:10.1248/cpb.54.163

Reference yield:

tert-butyl 3-hydroxyazetidine-1-carboxylate (141699-55-0) → tert-butyl 3-[4-nitro-3-(trimethylsilylmethyl)phenoxy]azetidine-1-carboxylate (319451-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / N,N-dimethyl-acetamide / 0.25 h / 20 °C

1.2: 95 percent / N,N-dimethyl-acetamide / 4 h / 20 °C

2.1: tetrahydrofuran; diethyl ether / 1 h / -5 °C

2.2: 46 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / tetrahydrofuran; diethyl ether / 3.5 h / 0 °C

With sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl acetamide;

DOI:10.1248/cpb.54.163

upstream raw materials:

tert-butyl 3-(4-nitrophenoxy)azetidine-1-carboxylate

(trimethylsilyl)methylmagnesium chloride

4-Fluoronitrobenzene

tert-butyl 3-hydroxyazetidine-1-carboxylate

Downstream raw materials:

t-butyl 3-{3-[2-(7-cyanonaphthalen-2-yl)-2-hydroxyethyl]-4-nitrophenoxy}azetidine-1-carboxylate

t-butyl 3-{3-[2-(7-cyanonaphthalen-2-yl)-2-hydroxyethyl]-4-(ethanesulfonyl)aminophenoxy}azetidine-1-carboxylate

t-butyl 3-{4-amino-3-[2-(7-cyanonaphthalen-2-yl)-2-hydroxyethyl]phenoxy}azetidine-1-carboxylate