[2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone

Base Information

• Chemical Name: [2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone
• CAS No.: 851615-68-4
• Molecular Formula: C₂₄H₃₇NO₄Si
• Molecular Weight: 431.648

Synonyms:[2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone

Chemical Property of [2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone

Chemical Property:

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Technology Process of [2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone

There total 5 articles about [2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone 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: 77.0%

(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-(2-hydroxymethyl-cyclohexyl)-methanone (851615-67-3) + t-butyldimethylsiyl triflate (69739-34-0) → [2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone (851615-68-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1055/s-2005-862393

Reference yield:

2-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazole-1-carbonyl)-cyclohexanecarboxylic acid → [2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone (851615-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂; hexane / 16 h / -78 °C

2: 74 percent / Cp₂Zr(H)Cl / tetrahydrofuran / 0.5 h / 20 °C

3: 77 percent / 2,6-lutidine / CH₂Cl₂ / 16 h / 0 - 20 °C

With 2,6-dimethylpyridine; Schwartz's reagent; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-2005-862393

Reference yield:

(-)-(1'R,2'S,3aS,9bR)-methyl 2'-(3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-1'-yl)cyclohexanecarboxylate (851615-60-6) → [2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-methanone (851615-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / Cp₂Zr(H)Cl / tetrahydrofuran / 0.5 h / 20 °C

2: 77 percent / 2,6-lutidine / CH₂Cl₂ / 16 h / 0 - 20 °C

With 2,6-dimethylpyridine; Schwartz's reagent; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2005-862393

upstream raw materials:

(3a,9b-dihydro-3H,4H-chromeno[4,3-c]isoxazol-1-yl)-(2-hydroxymethyl-cyclohexyl)-methanone

t-butyldimethylsiyl triflate

(-)-(1'R,2'S,3aS,9bR)-methyl 2'-(3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-1'-yl)cyclohexanecarboxylate

<3aS, 9bR>-(+)-1,3a-4,9a-tetrahydro-cis-3H-<1>benzopyrano<4,3-c>isoxazole

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