(1’S,2S)-2-(1’,2’-Dihydroxyethyl)-6-fluorochromane

Base Information

• Chemical Name: (1’S,2S)-2-(1’,2’-Dihydroxyethyl)-6-fluorochromane
• CAS No.: 905454-57-1
• Molecular Formula: C11H13FO3
• Molecular Weight: 212.221
• Mol file: 905454-57-1.mol

Synonyms:(1’S,2S)-2-(1’,2’-Dihydroxyethyl)-6-fluorochromane;(1S)-1-[(2S)-6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-1,2-ethanediol

Chemical Property of (1’S,2S)-2-(1’,2’-Dihydroxyethyl)-6-fluorochromane

Chemical Property:

• PSA: 49.69000
• LogP: 0.87250
• Solubility.: Dimethylformamide, Methanol

Purity/Quality:

98% or more ^*data from raw suppliers

(1’S,2S)-2-(1’,2’-Dihydroxyethyl)-6-fluorochromane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1’S,2S)-2-(1’,2’-Dihydroxyethyl)-6-fluorochromane

There total 3 articles about (1’S,2S)-2-(1’,2’-Dihydroxyethyl)-6-fluorochromane 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:

C11H11FO3 (1421916-54-2) → 1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol (905454-57-1) + 1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1R)-1,2-ethylene glycol (303176-39-8)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; hexane; at 20 ℃; for 0.5h; Overall yield = 18 g; Inert atmosphere;

Reference yield:

(S)-ethyl 6-fluorochroman-2-carboxylate (1335103-90-6,99199-61-8) → 1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol (905454-57-1) + 1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1R)-1,2-ethylene glycol (303176-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -100 - -78 °C / Inert atmosphere

1.2: -100 - -20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran; hexane / 0.5 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; n-butyllithium; In tetrahydrofuran; hexane;

Reference yield:

[1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene (793669-26-8,876514-31-7) → 1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol (905454-57-1) + 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran (197706-50-6,793669-26-8,876514-31-7)

Guidance literature:

[1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene; With oxygen; 4-nitro-benzoic acid; [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); In tert-butyl methyl ether; toluene; at 20 ℃; for 1h; Resolution of racemate;

With water; In tert-butyl methyl ether; toluene; at 25 ℃; for 18h; Product distribution / selectivity;

upstream raw materials:

[1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene

(S)-ethyl 6-fluorochroman-2-carboxylate

C₁₁H₁₁FO₃

Downstream raw materials:

1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1R)-1,2-ethylene glycol

(S,S)-(+)-α-[(p-toluenesulfonyloxy)methyl](6-fluoro-2-chromanyl)methanol

Refernces

• 1、 -. "PROCESS FOR PREPARING NEBIVOLOL". Page/Page column 23. . Retrieved 2008/12/06.