1236049-43-6

Basic information

• Product Name: (2S)-Hydroxy(phenyl)acetic acid - (3R)-3-amino-1-butanol (1:1)
• Synonyms: (S)-3-amino-1-butanol (R)-mandelic acid salt
• CAS NO: 1236049-43-6
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.287
• EINECS: 810-156-9
• Mol File: 1236049-43-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2S)-Hydroxy(phenyl)acetic acid - (3R)-3-amino-1-butanol (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-Hydroxy(phenyl)acetic acid - (3R)-3-amino-1-butanol (1:1)(1236049-43-6)
• EPA Substance Registry System: (2S)-Hydroxy(phenyl)acetic acid - (3R)-3-amino-1-butanol (1:1)(1236049-43-6)

Safety Data

• Hazardous Substances Data: 1236049-43-6(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Upstream product

• 61477-40-5 (R)-3-amino-1-butanol 
• 17199-29-0 (S)-Mandelic acid 
• 2867-59-6 2-aminobutanol 
• 611-71-2 (R)-Mandelic Acid 

Downstream Products

• 61477-40-5 (R)-3-amino-1-butanol 

Relevant articles and documents

Process Development Overcomes a Challenging Pd-Catalyzed C-N Coupling for the Synthesis of RORc Inhibitor GDC-0022

Process development for a multi-kilogram-scale synthesis of GDC-0022, an inhibitor of retinoic acid receptor-related orphan receptor γ(RORc), is described. Delivery of the active pharmaceutical ingredient (API) relied on diastereoselective preparation of a six-membered sultam building block, as well as execution of its benzylation under heterogeneous conditions. Investigation and optimization of a challenging late-stage palladium-catalyzed C-N coupling of a bicyclic amine were likewise central to synthetic efforts. Understanding of this key reaction, as well as the development of API salt forms and isolations, ultimately enabled a successful reaction at 8.0 kg scale, utilizing 1.0 mol % XantPhos-Pd-G2 as precatalyst and, in turn, preparation of >5.0 kg of GDC-0022 tosylate salt for preclinical needs.

Method for preparing (R)-3-aminobutanol

The invention provides a method for preparing (R)-3-aminobutanol, and the method comprises the following steps of: (1) providing 4-hydroxy-2-butanone and carrying out ammoniation reduction on the 4-hydroxy-2-butanone to obtain racemic 3-aminobutanol; (2) reacting (S)-mandelic acid with the racemic 3-aminobutanol to obtain resolved mandelic acid salt; and (3) alkalizing the resolved mandelic acid salt to obtain the product (R)-3-aminobutanol. According to the invention, the process of preparing the (R)-3-aminobutanol through reductive amination and salification resolution is simple and convenient to operate, low in reaction danger and pollution; the purity of the obtained (R)-3-aminobutanol reaches 99.9% (GC method).

SEPARATION OF AN ENANTIOMER MIXTURE OF (R)- AND (S)-3-AMINO-1-BUTANOL

The present invention relates to a process for separating an enantiomer mixture of (R)- and (S)-3-amino-1-butanol optionally protected on the oxygen atom, and to a process for preparing essentially enantiomerically pure (R)-3-amino-1-butanol which optionally bears a protecting group on the oxygen atom.