(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

Base Information

Chemical Name:(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone
CAS No.:623583-12-0
Molecular Formula:C₁₂H₁₃FN₄O₂
Molecular Weight:264.259
Hs Code.:

Synonyms:(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

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Chemical Property of (2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

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Technology Process of (2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

There total 5 articles about (2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone 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: 66.0%

: 31162-13-7
2-azidobenzoic acid

: ((2S,4R)-4-fluoropyrrolidin-2-yl)methanol hydrochloride

: 623583-12-0
(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

Guidance literature:: 2-azidobenzoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

((2S,4R)-4-fluoropyrrolidin-2-yl)methanol hydrochloride; With triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1016/j.tetlet.2003.08.075

Reference yield:

: 74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9
(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

: 623583-12-0
(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81 percent / DAST / CH₂Cl₂ / -78 - 20 °C

2.1: DIBAL-H / tetrahydrofuran / -78 - 20 °C

3.1: HCl; water / dioxane

4.1: (COCl)2; DMF / CH₂Cl₂

4.2: 66 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

With hydrogenchloride; oxalyl dichloride; water; diisobutylaluminium hydride; N,N-dimethyl-formamide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1016/j.tetlet.2003.08.075

Reference yield:

: 51-35-4,30724-02-8
4R-4-hydroxyproline

: 623583-12-0
(2-Azido-phenyl)-((2S,4R)-4-fluoro-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaOH; water / tetrahydrofuran / 0 °C

1.2: DEAD; PPh₃ / tetrahydrofuran / 0 - 20 °C

1.3: Amberlyst-15(R) / methanol / 20 °C

2.1: 81 percent / DAST / CH₂Cl₂ / -78 - 20 °C

3.1: DIBAL-H / tetrahydrofuran / -78 - 20 °C

4.1: HCl; water / dioxane

5.1: (COCl)2; DMF / CH₂Cl₂

5.2: 66 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

With hydrogenchloride; sodium hydroxide; oxalyl dichloride; water; diisobutylaluminium hydride; N,N-dimethyl-formamide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1.2: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2003.08.075