(1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ⁴-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ⁴-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester
• CAS No.: 93062-08-9
• Molecular Formula: C₁₀H₁₄N₂O₄S
• Molecular Weight: 258.298

Synonyms:(1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ⁴-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester

Chemical Property of (1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ⁴-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ⁴-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester

There total 1 articles about (1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ⁴-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-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: 42.0%

N1,N2-bis(methoxycarbonyl)sulfur diimide (16762-82-6) + cyclohexa-1,3-diene (1165952-91-9) → C10H14N2O4S (93062-10-3) + (3aS,7aR)-3a,4,5,7a-Tetrahydro-benzo[1,2,5]thiadiazole-1,3-dicarboxylic acid dimethyl ester (93062-09-0) + (1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ4-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester (93062-08-9)

Guidance literature:

In benzene; for 14h; Ambient temperature;

DOI:10.1021/ja00337a037

Reference yield: 100.0%

(1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ4-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester (93062-08-9) → C10H14N2O4S (93062-10-3)

Guidance literature:

In benzene; for 2h; Heating;

DOI:10.1021/ja00337a037

Reference yield:

(1R,4S)-2-[(E)-Methoxycarbonylimino]-2λ4-thia-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid methyl ester (93062-08-9) → (+/-)-cis-3,4-bis<(methoxycarbonyl)amino>cyclohexene (93062-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; tetrahydrofuran / 0.33 h / -60 °C

2: P(OMe)3 / methanol / 0.5 h / Heating

With phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/ja00337a037

upstream raw materials:

N¹,N²-bis(methoxycarbonyl)sulfur diimide

cyclohexa-1,3-diene

Downstream raw materials:

C₁₀H₁₄N₂O₄S

(+/-)-5-<(methoxycarbonyl)amino>-1,3-cyclohexadiene

(+/-)-cis-3,4-bis<(methoxycarbonyl)amino>cyclohexene

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