(2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol

Base Information

• Chemical Name: (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol
• CAS No.: 1383476-02-5
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 1383476-02-5.mol

Synonyms:(2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol

Chemical Property of (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol

There total 6 articles about (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol 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: 92.0%

(1S)-N-benzyl-1-[(4R)-2-(4-methoxyphenyl)-1,3-dioxolan-4-yl]ethanamine → (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol (1383476-02-5)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - -40 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0031-1289746

Reference yield:

(2R,3S)-3-(dibenzylamino)butane-1,2-diol → (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol (1383476-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / toluene / 20 h / Reflux; Inert atmosphere

2: N-iodo-succinimide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere; Molecular sieve

3: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 - -40 °C / Inert atmosphere

With N-iodo-succinimide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In dichloromethane; toluene;

DOI:10.1055/s-0031-1289746

Reference yield:

(2R,3S)-3-(dibenzylamino)-1-[(R)-p-tolylsulfinyl]butan-2-ol (1279699-93-2) → (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol (1383476-02-5)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium acetate / 6 h / 130 °C / Inert atmosphere

2: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C / Inert atmosphere

3: toluene-4-sulfonic acid / toluene / 20 h / Reflux; Inert atmosphere

4: N-iodo-succinimide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere; Molecular sieve

5: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 - -40 °C / Inert atmosphere

With N-iodo-succinimide; lithium aluminium tetrahydride; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; toluene; 1: Pummerer rearrangement;

DOI:10.1055/s-0031-1289746

upstream raw materials:

(S)-3-(dibenzylamino)-1-[(R)-p-tolylsulfinyl]butan-2-one

(2R,3S)-3-(dibenzylamino)-1-[(R)-p-tolylsulfinyl]butan-2-ol

dibenzylamine

Downstream raw materials:

(2S,3S)-1-benzyl-2-{[(4-methoxybenzyl)oxy]methyl}-3-methylaziridine