(1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ⁴-selena-tricyclo[5.2.1.0^1,5]decane

Base Information

• Chemical Name: (1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ⁴-selena-tricyclo[5.2.1.0^1,5]decane
• CAS No.: 176244-03-4
• Molecular Formula: C₁₇H₂₃ClO₂Se
• Molecular Weight: 373.781

Synonyms:(1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ⁴-selena-tricyclo[5.2.1.0^1,5]decane

Chemical Property of (1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ⁴-selena-tricyclo[5.2.1.0^1,5]decane

Chemical Property:

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Technology Process of (1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ⁴-selena-tricyclo[5.2.1.0^1,5]decane

There total 6 articles about (1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ⁴-selena-tricyclo[5.2.1.0^1,5]decane 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: 100.0%

(1S,2R,4R)-1-(4-Methoxy-phenylselanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol (176244-01-2) → (1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ4-selena-tricyclo[5.2.1.01,5]decane (176244-03-4)

Guidance literature:

With tert-butylhypochlorite; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00546-2

Reference yield:

(1S,4R)-1-(bromomethyl)-7,7-dimethylbicyclo-[2.2.1]heptan-2-one (64161-50-8) → (1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ4-selena-tricyclo[5.2.1.01,5]decane (176244-03-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / tetrahydrofuran; pentane / 12 h / Heating

2: 3.57 g / LiAlH₄ / diethyl ether / 0.67 h / -20 °C

3: t-BuOCl / CH₂Cl₂; methanol / 0.08 h / 0 °C

With lithium aluminium tetrahydride; tert-butylhypochlorite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane;

DOI:10.1016/S0957-4166(97)00423-0

Reference yield:

Lithium; 4-methoxy-benzeneselenolate (80095-52-9) → (1S,3R,5R,7R)-3-Chloro-3-(4-methoxy-phenyl)-10,10-dimethyl-4-oxa-3λ4-selena-tricyclo[5.2.1.01,5]decane (176244-03-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / tetrahydrofuran; pentane / 12 h / Heating

2: 3.57 g / LiAlH₄ / diethyl ether / 0.67 h / -20 °C

3: t-BuOCl / CH₂Cl₂; methanol / 0.08 h / 0 °C

With lithium aluminium tetrahydride; tert-butylhypochlorite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane;

DOI:10.1016/S0957-4166(97)00423-0

upstream raw materials:

(1S,2R,4R)-1-(4-Methoxy-phenylselanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol

(1S,4R)-1-(bromomethyl)-7,7-dimethylbicyclo-[2.2.1]heptan-2-one

Lithium; 4-methoxy-benzeneselenolate

(1S,4R)-1-(4-Methoxy-phenylselanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one

Downstream raw materials:

(1S,R_Se)-10-(p-methoxyphenylseleninyl)-2-exo-borneol

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