benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

Base Information

Chemical Name:benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate
CAS No.:1443769-13-8
Molecular Formula:C₁₅H₁₅NO₄
Molecular Weight:273.288
Hs Code.:

Synonyms:benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

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Chemical Property of benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

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Technology Process of benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

There total 3 articles about benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate 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:

: 1443768-72-6
(4S,5S)-N-benzyloxycarbonyl-4-vinyl-5-allyl-1,3-oxazinan-6-one

: 1443768-77-1
(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

: 1443769-13-8
benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; for 2h; Overall yield = 17 %; Inert atmosphere; Reflux;
DOI:10.1016/j.tet.2013.05.016

Reference yield:

: 3-([(benzyloxy)carbonyl]amino)-4-pentenoic acid

: 1443768-77-1
(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

: 1443769-13-8
benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: camphor-10-sulfonic acid / toluene / 90 °C / Molecular sieve; Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.67 h / -78 °C / Inert atmosphere

2.2: -78 - -40 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; camphor-10-sulfonic acid; potassium hexamethylsilazane; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2013.05.016

Reference yield:

: N-benzyloxycarbonyl-4-vinyl-1,3-oxazinan-6-one

: 1443768-77-1
(4aS,7aS)-N-benzyloxycarbonyl-4,4a,5,7a-tetrahydro-2H-cyclopenta[d][1,3]oxazinan-4-one

: 1443769-13-8
benzyl (4aS,7aS) 4-oxo-4,4a,7,7a-tetrahydrocyclopenta[d][1,3]oxazine-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.67 h / -78 °C / Inert atmosphere

1.2: -78 - -40 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium hexamethylsilazane; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2013.05.016