tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Base Information

• Chemical Name: tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate
• CAS No.: 1227472-26-5
• Molecular Formula: C₂₀H₂₆F₃NO₄
• Molecular Weight: 401.426
• Mol file: 1227472-26-5.mol

Synonyms:tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Chemical Property of tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

There total 7 articles about tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (3RS)-3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane hydrochloride (1227472-25-4) → tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (1227472-26-5)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 2h;

Reference yield:

tert-butyl 3-bromo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (898157-46-5) + (3-(trifluoromethoxy)phenyl)boronic acid (179113-90-7) → tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (1227472-26-5)

Guidance literature:

With sodium hexamethyldisilazane; nickel(II) iodide; R,S-trans-2-aminocyclohexan-1-ol; In isopropyl alcohol; at 70 ℃; Inert atmosphere;

Reference yield:

tert-butyl 3-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (954236-44-3) → tert-butyl 3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (1227472-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 0 °C

2: carbon tetrabromide; triphenylphosphine / tetrahydrofuran

3: nickel(II) iodide; lithium hexamethyldisilazane / isopropyl alcohol

With nickel(II) iodide; sodium tetrahydroborate; carbon tetrabromide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; isopropyl alcohol; 3: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.08.048

upstream raw materials:

tert-butyl 3-bromo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

(3-(trifluoromethoxy)phenyl)boronic acid

di-tert-butyl dicarbonate

(3RS)-3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane hydrochloride

Downstream raw materials:

(3RS)-N-(3,4-dimethylisoxazol-5-yl)-3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxamide

C₁₅H₁₈F₃NO₂

tert-butyl (3R)-3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

tert-butyl (3S)-3-[3-(trifluoromethoxy)phenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate