(1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one

Base Information

Chemical Name:(1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one
CAS No.:212896-19-0
Molecular Formula:C₁₆H₁₉NO₂
Molecular Weight:257.332
Hs Code.:

Synonyms:(1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one

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Chemical Property of (1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one

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Technology Process of (1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one

There total 8 articles about (1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-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: 52.0%

: 1774-47-6
trimethylsulfoxonium iodide

: 212896-14-5
(6S)-3-[(Z)-ethylidene]-6-isopropyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one

: 212896-19-0
(1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/jo991736l

Reference yield: 52.0%

: 1774-47-6
trimethylsulfoxonium iodide

: 212896-14-5
(6S)-3-[(Z)-ethylidene]-6-isopropyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one

: 212896-19-0
(1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one

: (1S,3R,6S)-6-Isopropyl-1-methyl-5-phenyl-7-oxa-4-aza-spiro[2.5]oct-4-en-8-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 1h; Ambient temperature;
DOI:10.1016/S0957-4166(98)00244-4

Reference yield:

: 17407-55-5
(S)-2-Hydroxy-3-methylbutanoic acid

: 212896-19-0
(1R,3S,6S)-6-isopropyl-1-methyl-7-phenyl-5-oxa-8-azaspiro[2.5]oct-7-en-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / DCC; BtOH; iPr₂NEt / tetrahydrofuran / -20 - 20 °C

2: 70 percent / tetrahydrofuran; diethyl ether / 0 - 20 °C

3: 80 percent / DCC; DMAP / CH₂Cl₂ / 20 °C

4: HCl / ethyl acetate / 1 h

5: Me₃N / CH₂Cl₂ / 1 h

6: 50 percent / K₂CO₃; TBAB / acetonitrile / 12 h / 20 °C

7: 52 percent / NaH / dimethylformamide / 1 h / 20 °C

With hydrogenchloride; dmap; tetrabutylammomium bromide; sodium hydride; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trimethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Grignard reaction / 3: Esterification / 4: Boc-deprotection / 5: Cyclization / 6: Condensation / 7: Cycloaddition;
DOI:10.1021/jo991736l