(S,S)-pseudoephedrine D-pipecolinamide

Base Information

• Chemical Name: (S,S)-pseudoephedrine D-pipecolinamide
• CAS No.: 170642-32-7
• Molecular Formula: C₁₆H₂₄N₂O₂
• Molecular Weight: 276.379
• Mol file: 170642-32-7.mol

Synonyms:(S,S)-pseudoephedrine D-pipecolinamide

Chemical Property of (S,S)-pseudoephedrine D-pipecolinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-pseudoephedrine D-pipecolinamide

There total 12 articles about (S,S)-pseudoephedrine D-pipecolinamide 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:

o-Methoxybenzyl bromide (52289-93-7) → (S,S)-pseudoephedrine D-pipecolinamide (170642-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA, LiCl, 3.) aq. NaOH, 4.) aq. sodium bicarbonate

2: 1.) n-BuLi, LiCl

3: 1.) n-BuLi, LiCl

With sodium hydroxide; n-butyllithium; sodium hydrogencarbonate; lithium chloride; lithium diisopropyl amide;

DOI:10.1021/ja00137a034

Reference yield:

pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → (S,S)-pseudoephedrine D-pipecolinamide (170642-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: n-BuLi, LiCl / hexane; tetrahydrofuran / 1 h / 0 °C

2: n-BuLi, LiCl / tetrahydrofuran; hexane / 1.67 h / 0 °C

3: 457 mg / CHCl₃ / 5 h / 48 °C

With n-butyllithium; lithium chloride; In tetrahydrofuran; hexane; chloroform;

DOI:10.1021/ja9624073

Reference yield:

(R)-2-Amino-6-chloro-hexanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide → (S,S)-pseudoephedrine D-pipecolinamide (170642-32-7)

Guidance literature:

In chloroform; at 48 ℃; for 5h;

DOI:10.1021/ja9624073

upstream raw materials:

1-chloro 4-iodobutane

2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide

pseudoephedrine

{[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-methyl}-carbamic acid tert-butyl ester

Downstream raw materials:

(R)-(+)-pipecolic acid

N-BOC-D-pipecolic acid