methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate

Base Information

• Chemical Name: methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate
• CAS No.: 1009051-63-1
• Molecular Formula: C₁₆H₁₇NO₅
• Molecular Weight: 303.315

Synonyms:methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate

Chemical Property of methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate

Chemical Property:

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Technology Process of methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate

There total 1 articles about methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-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:

(4R)-1,6-dioxo-4-phenyl-1,3,4,6,7,8-hexahydropyrido[2, 1-c][1,4]oxazine-9-carboxylic acid methyl ester (1009051-59-5) → methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate (1009051-63-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 18h; under 2585.81 Torr; Inert atmosphere;

DOI:10.1002/cmdc.201300525

Reference yield: 98.0%

methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate (1009051-63-1) → N-(1R-phenyl-2-hydroxyethyl)-2S,3R-bis(hydroxymethyl)piperidine (1034128-97-6)

Guidance literature:

methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 22h; Heating / reflux;

With sodium hydroxide; water; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

Reference yield:

methyl (4R,9R,9aS)-1,6-dioxo-4-phenyl-3,4,7,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazine-9-carboxylate (1009051-63-1) → methyl (4R,9R,9aS)-1-oxo-4-phenyl-octahydropyrido[2,1-c]morpholin-9-carboxylate (1009051-60-8)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at -20 - 20 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1002/cmdc.201300525

upstream raw materials:

(4R)-1,6-dioxo-4-phenyl-1,3,4,6,7,8-hexahydropyrido[2, 1-c][1,4]oxazine-9-carboxylic acid methyl ester

Downstream raw materials:

N-(1R-phenyl-2-hydroxyethyl)-2S,3R-bis(hydroxymethyl)piperidine

methyl (4R,9R,9aS)-1-oxo-4-phenyl-octahydropyrido[2,1-c]morpholin-9-carboxylate

2-benzyl 1-tert-butyl 3-methyl (2S,3R)-piperidin-1,2,3-tricarboxylate

(2S,3R)-2-[(benzyloxy)carbonyl]-1-[(tert-butoxy)carbonyl]piperidin-3-carboxylic acid

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