(1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.0^2,4]octane

Base Information

• Chemical Name: (1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.0^2,4]octane
• CAS No.: 861220-19-1
• Molecular Formula: C₁₆H₁₉BrO
• Molecular Weight: 307.23

Synonyms:(1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.0^2,4]octane

Chemical Property of (1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.0^2,4]octane

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Technology Process of (1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.0^2,4]octane

There total 4 articles about (1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.0^2,4]octane 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:

(1S,4R)-3-(2-Bromo-ethyl)-2-methyl-1-phenyl-bicyclo[2.2.1]hept-2-ene → (1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.02,4]octane (861220-19-1)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/ol051141e

Reference yield:

C16H20O (861220-06-6) → (1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.02,4]octane (861220-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr

2: m-CPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

With hydrogen bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ol051141e

Reference yield:

(1R,2S,4R,7R)-7-Bromomethyl-1,7-dimethyl-2-phenyl-bicyclo[2.2.1]heptan-2-ol (861220-01-1) → (1S,2R,4S,5R)-4-(2-Bromo-ethyl)-2-methyl-1-phenyl-3-oxa-tricyclo[3.2.1.02,4]octane (861220-19-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / t-BuOK / dimethylsulfoxide / 70 °C

2: HBr

3: m-CPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

With potassium tert-butylate; hydrogen bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ol051141e

upstream raw materials:

C₁₆H₂₀O

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

(1R,4R,7R)-9-bromocamphor

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