(1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester
• CAS No.: 515821-69-9
• Molecular Formula: C₂₆H₂₃NO₅
• Molecular Weight: 429.472

Synonyms:(1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester

Chemical Property of (1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester

There total 2 articles about (1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester 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:

methanol (67-56-1) + (2R,3R)-2,3-diacetoxy-N-benzhydryl-N-(2-oxo-2-phenylethyl)succinamic acid (515821-68-8) → (4-benzhydryl-3-oxo-6-phenyl-3,4-dihydro-2H-[1,4]oxazin-2-yl)hydroxyacetic acid methyl ester + (1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester (515821-69-9)

Guidance literature:

methanol; (2R,3R)-2,3-diacetoxy-N-benzhydryl-N-(2-oxo-2-phenylethyl)succinamic acid; With thionyl chloride; at 60 ℃; for 2h;

With sulfuric acid; silica gel; In toluene; for 0.25h; Heating;

DOI:10.1016/S0040-4020(02)01297-8

Reference yield:

2-(benzhydrylamino)-1-phenyl-1-ethanone (23934-75-0) → (1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester (515821-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CH₂Cl₂ / 0 - 30 °C

2.1: thionyl chloride / 2 h / 60 °C

2.2: 65.0 g / TFA / CH₂Cl₂ / 3 h / -10 °C

With thionyl chloride; In dichloromethane;

DOI:10.1016/S0040-4020(02)01297-8

Reference yield: 70.0%

(1R,5S,7R)-3-benzhydryl-2-oxo-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester (515821-69-9) → (1S,5S,7R)-3-benzhydryl-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester (515821-71-3)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(02)01297-8

upstream raw materials:

methanol

(2R,3R)-2,3-diacetoxy-N-benzhydryl-N-(2-oxo-2-phenylethyl)succinamic acid

2-(benzhydrylamino)-1-phenyl-1-ethanone

Downstream raw materials:

(1S,5S,7R)-3-benzhydryl-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester

(1S,5S,7R)-5-Phenyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid methyl ester

(1S,5S,7R)-3-(tert-butoxycarbonyl)-5-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic acid methyl ester

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