(1S^*,3R^*,5S^*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane

Base Information

• Chemical Name: (1S^*,3R^*,5S^*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane
• CAS No.: 118724-78-0
• Molecular Formula: C₁₇H₂₄BrNO₂
• Molecular Weight: 354.287

Synonyms:(1S^*,3R^*,5S^*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane

Chemical Property of (1S^*,3R^*,5S^*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane

Chemical Property:

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Technology Process of (1S^*,3R^*,5S^*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane

There total 1 articles about (1S^*,3R^*,5S^*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane 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: 63.0%

(1S,3S,5R)-5-(3-Methoxy-phenyl)-8-methyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-2-oxa-8-aza-bicyclo[3.3.1]nonane; hydrochloride (118916-31-7) → (1S*,3R*,5S*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane (118724-78-0)

Guidance literature:

With bromine; triphenylphosphine; In tetrahydrofuran; at 10 - 20 ℃; for 0.25h;

DOI:10.1021/jo00267a039

Reference yield:

(1S*,3R*,5S*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane (118724-78-0) → 2-methyl-4aα-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8aα-decahydro-6α-isoquinolinol (61528-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: TFA / 1 h / Ambient temperature

2: K₂CO₃ / acetonitrile / 2 h / Ambient temperature

3: 90 percent / K₂CO₃, MeOH / 24 h / Ambient temperature

4: 68 percent / H₂ / PtO₂ / ethanol; acetic acid / 16 h / 3102.9 Torr

With methanol; hydrogen; potassium carbonate; trifluoroacetic acid; platinum(IV) oxide; In ethanol; acetic acid; acetonitrile;

DOI:10.1021/jo00267a039

Reference yield:

(1S*,3R*,5S*)-3-(2-bromoethyl)-5-(3-methoxyphenyl)-8-methyl-2-oxa-8-azabicyclo<3.3.1>nonane (118724-78-0) → 2-methyl-4aα-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8aβ-decahydro-6α-isoquinolinol (61528-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: TFA / 1 h / Ambient temperature

2: K₂CO₃ / acetonitrile / 2 h / Ambient temperature

3: 90 percent / K₂CO₃, MeOH / 24 h / Ambient temperature

4: 82 percent / H₂ / PtO₂ / ethanol / 16 h / 3102.9 Torr

With methanol; hydrogen; potassium carbonate; trifluoroacetic acid; platinum(IV) oxide; In ethanol; acetonitrile;

DOI:10.1021/jo00267a039

upstream raw materials:

(1S,3S,5R)-5-(3-Methoxy-phenyl)-8-methyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-2-oxa-8-aza-bicyclo[3.3.1]nonane; hydrochloride

Downstream raw materials:

Acetic acid (S)-3-bromo-1-[(R)-4-(3-methoxy-phenyl)-1-methyl-1,2,3,4-tetrahydro-pyridin-4-ylmethyl]-propyl ester

2-methyl-4aα-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8aα-decahydro-6α-isoquinolinol

2-methyl-4aα-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8aβ-decahydro-6α-isoquinolinol

2-methyl-4aα-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8aα-decahydro-6-oxoisoquinoline

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