(1R^*,3S^*,4S^*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene

Base Information

• Chemical Name: (1R^*,3S^*,4S^*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene
• CAS No.: 142003-66-5
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412

Synonyms:(1R^*,3S^*,4S^*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene

Chemical Property of (1R^*,3S^*,4S^*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene

Chemical Property:

Purity/Quality:

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Technology Process of (1R^*,3S^*,4S^*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene

There total 5 articles about (1R^*,3S^*,4S^*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene 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%

(1R*,3S*,4S*,7S*,8S*)-2-benzoyl-3-(1-propyl)-5,5-dimethoxy-7,8-bis(phenylsulfonyl)-2-azabicyclo<2.2.2>octane (142003-65-4) → (1R*,3S*,4S*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene (142003-66-5)

Guidance literature:

With sodium amalgam; In tetrahydrofuran; methanol; at -30 ℃; for 0.5h;

DOI:10.1021/jo00041a012

Reference yield:

4-methoxypyridine (620-08-6,1232006-56-2) → (1R*,3S*,4S*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene (142003-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) THF, a) -78 deg C, 15 min, b) to -20 deg C, 10 min, 2) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h

2: benzene; tetrahydrofuran / 66 h / 80 °C

3: 91 percent / (+/-)-10-camphorsulfonic acid / 62 h / Ambient temperature

4: 99 percent / Na(Hg) / methanol; tetrahydrofuran / 0.5 h / -30 °C

With sodium amalgam; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; benzene;

DOI:10.1021/jo00041a012

Reference yield:

benzoyl chloride (98-88-4) → (1R*,3S*,4S*)-2-benzoyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene (142003-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) THF, a) -78 deg C, 15 min, b) to -20 deg C, 10 min, 2) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h

2: benzene; tetrahydrofuran / 66 h / 80 °C

3: 91 percent / (+/-)-10-camphorsulfonic acid / 62 h / Ambient temperature

4: 99 percent / Na(Hg) / methanol; tetrahydrofuran / 0.5 h / -30 °C

With sodium amalgam; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; benzene;

DOI:10.1021/jo00041a012

upstream raw materials:

(1R^*,3S^*,4S^*,7S^*,8S^*)-2-benzoyl-3-(1-propyl)-5,5-dimethoxy-7,8-bis(phenylsulfonyl)-2-azabicyclo<2.2.2>octane

4-methoxypyridine

benzoyl chloride

(4-Methoxy-2-propyl-2H-pyridin-1-yl)-phenyl-methanone

Downstream raw materials:

(1R^*,3S^*,4S^*)-2-benzyl-3-(1-propyl)-8,8-dimethoxy-2-azabicyclo<2.2.2>oct-5-ene

(1R^*,3S^*,4S^*)-2-benzyl-3-(1-propyl)-2-azabicyclo<2.2.2>oct-7-en-5-one

(1R^*,3S^*,4S^*,5S^*)-2-benzyl-3-(1-propyl)-5-<(E)-2-(dimethylphenylsilyl)-1-ethenyl>-2-azabicyclo<2.2.2>oct-7-en-5-ol

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