(R)-N-Boc-2-Hydroxymethylmorpholine
[CAS# 135065-71-3]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (R)-N-Boc-2-Hydroxymethylmorpholine
• Synonyms: (R)-2-Hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester; 2-(Hydroxymethyl)morpholine-4-carboxylic acid (R)-tert-butyl ester
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• CAS Registry Number: 135065-71-3
• EC Number: 815-640-3
• SMILES: CC(C)(C)OC(=O)N1CCO[C@H](C1)CO

Properties

• Density: 1.118
• Boiling point: 321 °C
• Flash point: 148 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(R)-N-Boc-2-Hydroxymethylmorpholine is a notable chemical compound primarily utilized in organic synthesis and pharmaceutical development due to its unique structural properties. This compound, a derivative of morpholine, features a Boc (tert-butyloxycarbonyl) protecting group attached to a hydroxymethyl group at the 2-position of the morpholine ring.

The synthesis of (R)-N-Boc-2-Hydroxymethylmorpholine involves the reaction of morpholine with a Boc-protected hydroxymethylating agent. The Boc group serves as a protecting group for the amine function of the morpholine ring, which simplifies subsequent chemical reactions by preventing unwanted side reactions. The hydroxymethyl group, on the other hand, introduces a functional handle that can be modified further, making the compound versatile for various applications.

In the field of pharmaceuticals, (R)-N-Boc-2-Hydroxymethylmorpholine is employed as an intermediate in the synthesis of more complex molecules. Its ability to undergo further transformations makes it valuable for creating diverse chemical entities, including potential drug candidates. The morpholine ring is a key structural feature in many biologically active compounds, and the presence of the Boc group provides additional chemical stability during synthesis.

The compound's application extends to the development of chiral molecules and asymmetric synthesis. The (R)-configuration of the Boc-protected morpholine is crucial in creating enantiomerically pure substances, which is important for producing drugs with high efficacy and minimal side effects. The ability to control stereochemistry in synthesis processes is a significant advantage in the pharmaceutical industry.

In addition to its use in pharmaceuticals, (R)-N-Boc-2-Hydroxymethylmorpholine finds applications in material science and polymer chemistry. Its functional groups can be used to introduce morpholine units into polymer chains, potentially altering the properties of the resulting materials.

Overall, (R)-N-Boc-2-Hydroxymethylmorpholine is a valuable compound in organic synthesis due to its versatility and functionality. Its role in pharmaceutical development, chiral synthesis, and material science highlights its importance in various chemical applications.

References

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