(3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Base Information

Chemical Name:(3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate
CAS No.:1384579-02-5
Molecular Formula:C₂₅H₂₉NO₅
Molecular Weight:423.509
Hs Code.:

Synonyms:(3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

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Chemical Property of (3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

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Technology Process of (3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

There total 3 articles about (3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-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: 91.0%

: 1384579-00-3
benzyl allyl((R)-2-(benzyloxy)-1-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethyl)carbamate

: 1384579-02-5
(3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 4h; Reflux;
DOI:10.1016/j.tetasy.2012.04.017

Reference yield:

: 1214915-00-0
benzyl (R)-2-(benzyloxy)-1-((4S,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl) ethylcarbamate

: 1384579-02-5
(3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

2.1: water; acetic acid / 16 h / 20 °C

2.2: 0 °C / pH 7

3.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 3 h / Reflux

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Reflux

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; water; iodine; sodium hydride; acetic acid; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetasy.2012.04.017

Reference yield:

: 1384578-97-5
benzyl allyl((R)-2-(benzyloxy)-1-((4S,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethyl)carbamate

: 1384579-02-5
(3aR,4R,8aR)-benzyl 4-(benzyloxymethyl)-2,2-dimethyl-6,8a-dihydro-3aH-[1,3]dioxolo[4,5-c]azepine-5(4H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: water; acetic acid / 16 h / 20 °C

1.2: 0 °C / pH 7

2.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 3 h / Reflux

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

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; water; iodine; acetic acid; triphenylphosphine; In dichloromethane; toluene;
DOI:10.1016/j.tetasy.2012.04.017