1120335-12-7

Basic information

• Product Name: (S)-(4-benzylmorpholin-2-yl)(morpholino)methanone di-p-toluoyl-L-(-)-tartrate
• CAS NO: 1120335-12-7
• Molecular Weight: 676.72
• Mol File: 1120335-12-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-(4-benzylmorpholin-2-yl)(morpholino)methanone di-p-toluoyl-L-(-)-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(4-benzylmorpholin-2-yl)(morpholino)methanone di-p-toluoyl-L-(-)-tartrate(1120335-12-7)
• EPA Substance Registry System: (S)-(4-benzylmorpholin-2-yl)(morpholino)methanone di-p-toluoyl-L-(-)-tartrate(1120335-12-7)

Safety Data

• Hazardous Substances Data: 1120335-12-7(Hazardous Substances Data)

Upstream product

• 852237-40-2 (4-benzylmorpholin-2-yl)(morpholino)methanone 
• 32634-66-5 Di-p-toluoyl-L-tartaric acid 

Downstream Products

• 1120335-11-6 (S)-(4-benzylmorpholin-2-yl)(morpholino)methanone 

Relevant articles and documents

Practical synthesis of chiral 2-morpholine: (4-Benzylmorpholin-2-(s)-yl)- (tetrahydropyran-4-yl) Methanone mesylate, a useful pharmaceutical intermediate

A commercial synthesis was developed for the production of (4-benzylmorpholin-2-(S)-yl)-(tetrahydropyran-4-yl) methanone mesylate, la, a key starting material for a phase 2, new investigational drug candidate at Eli Lilly and Company. The target compound was produced in the clinical pilot plant by the combination of two key steps: resolution of a morpholine amide intermediate to install the S-morpholino stereocenter in 35% yield and a high-yielding (89%) Grignard reaction to generate the title compound la, isolated as a mesylate salt. The Grignard reaction was found to proceed optimally when using a combination of I2 and DIBAL-H for the initiation. In addition, the Grignard reagent formation was monitored by ReactMax calorimetry, and proof-of-concept studies were completed, demonstrating that the Grignard step could potentially be run as a continuous process with magnesium recycling.