(6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.0^3,7]tetradeca-1⁽¹⁴⁾,2,10,12-tetraen-4-one

Base Information

• Chemical Name: (6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.0^3,7]tetradeca-1⁽¹⁴⁾,2,10,12-tetraen-4-one
• CAS No.: 1365841-23-1
• Molecular Formula: C₃₀H₃₄F₃NO₃
• Molecular Weight: 513.6

Synonyms:(6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.0^3,7]tetradeca-1⁽¹⁴⁾,2,10,12-tetraen-4-one

Chemical Property of (6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.0^3,7]tetradeca-1⁽¹⁴⁾,2,10,12-tetraen-4-one

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Technology Process of (6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.0^3,7]tetradeca-1⁽¹⁴⁾,2,10,12-tetraen-4-one

There total 9 articles about (6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.0^3,7]tetradeca-1⁽¹⁴⁾,2,10,12-tetraen-4-one 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: 91.0%

(S)-(2-{[benzyl({[tris(propan-2-yl)silyl]oxy}carbonyl)amino]-methyl}-4-(trifluoromethyl)phenyl)[(5R)-5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-2-oxo-2,5-dihydrofuran-3-yl]methyl acetate → (6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.03,7]tetradeca-1(14),2,10,12-tetraen-4-one (1365841-23-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1021/jo3001657

Reference yield:

tert-butyl N-benzyl-N-{[2-ethenyl-5-(trifluoromethyl)-phenyl]methyl}carbamate (1365840-90-9) → (6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.03,7]tetradeca-1(14),2,10,12-tetraen-4-one (1365841-23-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / 1,1-dichloroethane / 4 h / 96 °C

2.1: osmium(VIII) oxide / tetrahydrofuran; water; toluene / 0.13 h

2.2: 1 h

3.1: n-butyllithium; diphenyl diselenide; lithium phenylselenide / tetrahydrofuran; hexane; acetonitrile / 8.17 h / -42 - -20 °C

4.1: pyridine; dmap / dichloromethane / 0.83 h / 0 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; n-butyllithium; diphenyl diselenide; lithium phenylselenide; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,1-dichloroethane; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo3001657

Reference yield:

tris(propan-2-yl)silyl N-benzyl-N-{[2-ethenyl-5-(trifluoromethyl)phenyl]methyl}carbamate (1365840-91-0) → (6R,7R)-8-benzyl-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-12-(trifluoromethyl)-5-oxa-8-azatricyclo-[8.4.0.03,7]tetradeca-1(14),2,10,12-tetraen-4-one (1365841-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: osmium(VIII) oxide / tetrahydrofuran; water; toluene / 0.13 h

1.2: 1 h

2.1: n-butyllithium; diphenyl diselenide; lithium phenylselenide / tetrahydrofuran; hexane; acetonitrile / 8.17 h / -42 - -20 °C

3.1: pyridine; dmap / dichloromethane / 0.83 h / 0 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; dmap; osmium(VIII) oxide; n-butyllithium; diphenyl diselenide; lithium phenylselenide; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo3001657

upstream raw materials:

(2-bromo-5-(trifluoromethyl)phenyl)methanamine

tert-butyl N-{[2-bromo-5-(trifluoromethyl)phenyl]methyl}-carbamate

tert-butyl N-{[2-ethenyl-5-(trifluoromethyl)phenyl]methyl}-carbamate

tert-butyl N-benzyl-N-{[2-ethenyl-5-(trifluoromethyl)-phenyl]methyl}carbamate

Downstream raw materials:

[(3R)-2-benzyl-3-(hydroxymethyl)-8-(trifluoromethyl)-2,3-di-hydro-1H-2-benzaze-pin-4-yl]methanol

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