threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane

Base Information

• Chemical Name: threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane
• CAS No.: 116782-56-0
• Molecular Formula: C₁₅H₂₀N₂O₄
• Molecular Weight: 292.335

Synonyms:threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane

Chemical Property of threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane

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Technology Process of threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane

There total 2 articles about threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane 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: 92.5%

(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (119-62-0,716-61-0,2792-51-0,2792-52-1,2964-48-9,3689-55-2,63526-31-8,71115-69-0,140694-64-0) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane (116782-56-0)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1002/1522-2675(200204)85:4<1062::AID-HLCA1062>3.0.CO;2-N

Reference yield:

(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (119-62-0,716-61-0,2792-51-0,2792-52-1,2964-48-9,3689-55-2,63526-31-8,71115-69-0,140694-64-0) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane (116782-56-0) + (S)-(4-Nitro-phenyl)-(S)-1-oxa-4-aza-spiro[4.5]dec-3-yl-methanol

Guidance literature:

In benzene; for 0.75h; Title compound not separated from byproducts; Heating;

DOI:10.1007/s10593-005-0067-x

Reference yield: 63.0%

phosgene (75-44-5) + threo-(2S,3S)-3-(hydroxymethyl)-2-(4-nitrophenyl)-1-oxa-4-azaspiro[4.5]decane (116782-56-0) → (5S,6S)-6-(4-nitrophenyl)-8-spirocyclohexyl-3,7-dioxa-1-azabicyclo[3.3.0]octan-2-one

Guidance literature:

With triethylamine; In tetrahydrofuran; toluene; at -20 ℃;

upstream raw materials:

(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol

cyclohexanone

Downstream raw materials:

(S)-[1,1']-binaphthalenyl-2,2'-diol

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