(1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester
• CAS No.: 127157-58-8
• Molecular Formula: C₁₇H₂₁NO₄Se
• Molecular Weight: 382.318
• Mol file: 127157-58-8.mol

Synonyms:(1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester

Chemical Property of (1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester

There total 2 articles about (1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl 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: 40.0%

Phenylselenyl chloride (5707-04-0) + 3,6-Dihydro-2H-pyridine-1,2-dicarboxylic acid 1-tert-butyl ester (90471-44-6) → (1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester (127157-58-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)76188-0

Reference yield:

(+/-)-baikiain hydrochloride (41994-52-9) → (1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester (127157-58-8)

Guidance literature:

Multi-step reaction with 2 steps

2: 40 percent / Et₃N / CH₂Cl₂ / 0 °C

With triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)76188-0

Reference yield:

(1R,4R,5R)-7-Oxo-4-phenylselanyl-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid tert-butyl ester (127157-58-8) → (2R,6S)-6-Benzyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid methyl ester; hydrochloride (127144-95-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) DMAP / 1.) t-BuOK / 1.) room temp., 5 min

2: 67 percent / mCPBA / 0 deg C --> room temp.

3: aluminium chloride / CH₂Cl₂; diethyl ether / 0.17 h / -15 °C

4: HCl / dioxane / 0.5 h / Ambient temperature

With hydrogenchloride; dmap; aluminium trichloride; 3-chloro-benzenecarboperoxoic acid; potassium tert-butylate; In 1,4-dioxane; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)76188-0

upstream raw materials:

Phenylselenyl chloride

3,6-Dihydro-2H-pyridine-1,2-dicarboxylic acid 1-tert-butyl ester

(+/-)-baikiain hydrochloride

Downstream raw materials:

(2S,4S,5S)-4-Acetoxy-5-phenylselanyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2R,6S)-6-Benzyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid methyl ester; hydrochloride

trans-6-benzyl-Δ⁴-pipecolate

(2S,6S)-6-Benzyl-3,6-dihydro-2H-pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester