(4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol

Base Information

Chemical Name:(4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol
CAS No.:1383736-66-0
Molecular Formula:C₁₆H₁₉NO₃
Molecular Weight:273.332
Hs Code.:

Synonyms:(4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol

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Chemical Property of (4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol

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Technology Process of (4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol

There total 6 articles about (4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol 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: 90.0%

: 1383736-65-9
(4R,5S,7R)-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-yl benzoate

: 1383736-66-0
(4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol301461e

Reference yield:

: 1383736-52-4
4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal

: 1383736-66-0
(4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

2.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

2.2: 12 h / 90 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); bromine; silica gel; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Aldol condensation;
DOI:10.1021/ol301461e

Reference yield:

: 1383736-54-6
1-((4R,5R)-5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazol-4-yl)ethanone

: 1383736-66-0
(4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone / ethyl acetate / -78 °C

1.2: 8 h / Inert atmosphere; Reflux

2.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

3.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

3.2: 12 h / 90 °C

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); bromine; silica gel; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 2.1: Aldol condensation;
DOI:10.1021/ol301461e