(1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]dec-2-ene

Base Information

• Chemical Name: (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]dec-2-ene
• CAS No.: 292039-13-5
• Molecular Formula: C₁₉H₂₅NO
• Molecular Weight: 283.414

Synonyms:(1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]dec-2-ene

Chemical Property of (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]dec-2-ene

Chemical Property:

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Technology Process of (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]dec-2-ene

There total 3 articles about (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.0^1,5]dec-2-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: 95.0%

benzyl bromide (100-39-0) + (1S,5R,7R)-10,10-dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.01,5]dec-2-ene (292039-09-9) → (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.01,5]dec-2-ene (292039-13-5)

Guidance literature:

(1S,5R,7R)-10,10-dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.0^1,5]dec-2-ene; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

benzyl bromide; In tetrahydrofuran;

DOI:10.1016/S0957-4166(00)00197-X

Reference yield:

(1S,4R)-1-amino-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one (38989-02-5) → (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.01,5]dec-2-ene (292039-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaBH₄

2.1: 95 percent / NaHCO₃ / CHCl₃ / 48 h / Heating

3.1: LDA / tetrahydrofuran / -78 °C

3.2: 95 percent / tetrahydrofuran

With sodium tetrahydroborate; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; chloroform; 1.1: Reduction / 2.1: cyclocondensation / 3.1: Metallation / 3.2: Alkylation;

DOI:10.1016/S0957-4166(00)00197-X

Reference yield:

(1S,2R,4R)-1-amino-2-exo-hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane (147168-89-6,793645-97-3) → (1S,5R,7R)-10,10-Dimethyl-3-((R)-1-methyl-2-phenyl-ethyl)-4-oxa-2-aza-tricyclo[5.2.1.01,5]dec-2-ene (292039-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / NaHCO₃ / CHCl₃ / 48 h / Heating

2.1: LDA / tetrahydrofuran / -78 °C

2.2: 95 percent / tetrahydrofuran

With sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; chloroform; 1.1: cyclocondensation / 2.1: Metallation / 2.2: Alkylation;

DOI:10.1016/S0957-4166(00)00197-X

upstream raw materials:

benzyl bromide

(1S,5R,7R)-10,10-dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.0^1,5]dec-2-ene

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

(1S,2R,4R)-1-amino-2-exo-hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane

Downstream raw materials:

2-methyl-3-phenylpropanoic acid

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