(4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one

Base Information

Chemical Name:(4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one
CAS No.:942598-45-0
Molecular Formula:C₁₆H₂₂N₂O₃S
Molecular Weight:322.428
Hs Code.:

Synonyms:(4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one

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Chemical Property of (4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one

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Technology Process of (4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one

There total 4 articles about (4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-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: 79.0%

: 942598-42-7
(R)-1-((1S,Z)-2-{[(R)-N-methylphenylsulfonimidoyl]methylene}cyclopentyl)ethanol

: 3019-71-4
Trichloroacetyl isocyanate

: 942598-45-0
(4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one

Guidance literature:: (R)-1-((1S,Z)-2-{[(R)-N-methylphenylsulfonimidoyl]methylene}cyclopentyl)ethanol; Trichloroacetyl isocyanate; In dichloromethane; for 5h;

With ammonium bicarbonate; In methanol; at 20 ℃; for 12h;

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; stereoselective reaction;
DOI:10.1002/ejoc.201400068

Reference yield:

: (R)-1-((1S,Z)-2-{[(R)-N-methylphenylsulfonimidoyl]methylene}cyclopentyl)ethyl carbamate

: 942598-45-0
(4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h;
DOI:10.1021/ol0706410

Reference yield:

: C₁₃H₁₇NOS

: 942598-45-0
(4R,4aS,7aR)-4-methyl-7a-(((R)-N-methyl-S-phenylsulfonimidoyl)methyl)-hexahydrocyclopent[d][1,3]oxazin-2(1H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: nBuLi / tetrahydrofuran / -78 °C

1.2: 78 percent / ClTi(OiPr)3 / tetrahydrofuran / -78 °C

2.1: CH₂Cl₂ / 3 h / 20 °C

2.2: (NH₄)2CO₃ / CH₂Cl₂; methanol / 12 h / 20 °C

3.1: 1.56 g / nBuLi / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0706410