1-AZETIDINECARBOXYLIC ACID, 2-[[[2-NITRO-3-PYRIDINYL]OXY]METHYL]-, 1,1-DIMETHYLETHYL ESTER, (2S)-

Base Information

• Chemical Name: 1-AZETIDINECARBOXYLIC ACID, 2-[[[2-NITRO-3-PYRIDINYL]OXY]METHYL]-, 1,1-DIMETHYLETHYL ESTER, (2S)-
• CAS No.: 209530-92-7
• Molecular Formula: C14H19N3O5
• Molecular Weight: 309.31800
• Mol file: 209530-92-7.mol

Synonyms:2-NITRO-AP;Nitro-AP;2-nitro-3-[2(S)-(N-tert-butoxycarbonyl)-2-azetidinylmethoxy]pyridine;

Chemical Property of 1-AZETIDINECARBOXYLIC ACID, 2-[[[2-NITRO-3-PYRIDINYL]OXY]METHYL]-, 1,1-DIMETHYLETHYL ESTER, (2S)-

Chemical Property:

• PSA: 97.48000
• LogP: 2.83910

Purity/Quality:

99% ^*data from raw suppliers

(2S)-2-[[[2-NITRO-3-PYRIDINYL]OXY]METHYL]-1-AZETIDINECARBOXYLIC ACID-1,1-DIMETHYLETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-AZETIDINECARBOXYLIC ACID, 2-[[[2-NITRO-3-PYRIDINYL]OXY]METHYL]-, 1,1-DIMETHYLETHYL ESTER, (2S)-

There total 4 articles about 1-AZETIDINECARBOXYLIC ACID, 2-[[[2-NITRO-3-PYRIDINYL]OXY]METHYL]-, 1,1-DIMETHYLETHYL ESTER, (2S)- 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%

3-hydroxy-2-nitropyridine (15128-82-2) + 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (161511-85-9) → 2-nitro-3-<2(S)-N-(tert-butoxycarbonyl)-2-azetidinylmethoxy>pyridine (209530-92-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jm9910223

Reference yield:

(S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid (51077-14-6) → 2-nitro-3-<2(S)-N-(tert-butoxycarbonyl)-2-azetidinylmethoxy>pyridine (209530-92-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / BH₃*DMS / tetrahydrofuran / -78 °C

2: 40 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / Ambient temperature

With dimethylsulfide borane complex; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jm9910223

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-nitro-3-<2(S)-N-(tert-butoxycarbonyl)-2-azetidinylmethoxy>pyridine (209530-92-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / aq. NaOH / dioxane

2: 89 percent / BH₃*DMS / tetrahydrofuran / -78 °C

3: 40 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / Ambient temperature

With sodium hydroxide; dimethylsulfide borane complex; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm9910223

upstream raw materials:

3-hydroxy-2-nitropyridine

2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

(S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid

Refernces

• 1、 Dolle, Frederic,Valette, Heric,Bottlaender, Michel,Hinnen, Francoise,Vaufrey, Francoise,Guenther, Ilonka,Crouzel, Christian. "Synthesis of 2-[18F]fluoro-3-[2(S)-2-azetidinylmethoxy]pyridine, a highly potent radioligand for in vivo imaging central nicotinic acetylcholine receptors". . p. 451 - 463. Retrieved 2007/10/03.