(-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

Base Information

Chemical Name:(-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one
CAS No.:244104-69-6
Molecular Formula:C₂₀H₂₅NO₃S
Molecular Weight:359.489
Hs Code.:

Synonyms:(-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

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Chemical Property of (-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

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Technology Process of (-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

There total 4 articles about (-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-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: 71.0%

: 6284-46-4
isopropyl crotonate

: 146860-26-6
(+)-(R_S)-3-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene

: 244104-69-6
(-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(99)01047-3

Reference yield: 70.0%

: 623-43-8
crotonic acid methyl ester

: 146860-26-6
(+)-(R_S)-3-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene

: 244104-69-6
(-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

: 244104-72-1
(-)-(Ss,7'S)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

Guidance literature:: (+)-(R_S)-3-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃;

crotonic acid methyl ester; In tetrahydrofuran; hexane; at 20 ℃; for 24h; Title compound not separated from byproducts;
DOI:10.1016/j.tetasy.2005.11.009

Reference yield:

: 1517-82-4
(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

: 244104-69-6
(-)-(Ss,7'R)-7'-methyl-8'-[(4-methylphenyl)sulfinyl]-6',7'-dihydrospiro[cyclohexane-1,3'-[1,3]oxazolo[3,4-a]pyridin]-5'(1'H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -78 °C

2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; 2: Michael reaction;
DOI:10.1016/S0957-4166(01)00553-5