N-Boc-L-alaninol
[CAS 79069-13-9]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: N-Boc-L-alaninol
• Synonyms: N-tert-Butoxycarbonyl-L-alaninol
• Molecular Formula: C₈H₁₇NO₃
• Molecular Weight: 175.22
• Protein Sequence: A
• CAS Registry Number: 79069-13-9
• EC Number: 807-439-4
• SMILES: C[C@@H](CO)NC(=O)OC(C)(C)C

Properties

• Density: 1.0$+/-$0.1 g/cm³ Calc.^*
• Melting point: 59 - 62 $degree$C (Expl.)
• Boiling point: 276.4$+/-$23.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 121.0$+/-$22.6 $degree$C (Calc.)^*
• Index of refraction: 1.45 (Calc.)^*
• alpha: -11 ° (c=1, chloroform)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

N-Boc-L-alaninol is a protected amino alcohol derived from the naturally occurring amino acid L-alanine. The compound belongs to a class of synthetic intermediates widely used in organic synthesis, peptide chemistry, and pharmaceutical research. Its structure contains a tert-butoxycarbonyl (Boc) protected amino group and a primary alcohol functionality, a combination that provides chemical stability while allowing selective transformations during multistep synthesis. Because of its well-defined stereochemistry inherited from L-alanine, N-Boc-L-alaninol has become an important chiral building block in modern synthetic chemistry.

The development of N-Boc-L-alaninol is closely connected to advances in amino acid chemistry and the introduction of protecting-group strategies. During the twentieth century, chemists recognized that amino acids and their derivatives could serve as valuable sources of chirality for the preparation of biologically active compounds. At the same time, the development of the Boc protecting group provided an effective method for temporarily masking amino functionality while preserving stereochemical integrity. The combination of these advances led to the widespread use of Boc-protected amino alcohols as versatile synthetic intermediates.

N-Boc-L-alaninol is typically prepared by reduction of appropriately protected alanine derivatives while maintaining the configuration of the stereogenic center. The Boc group protects the amino function from unwanted reactions, whereas the alcohol group remains available for selective modification. This balance of stability and reactivity has made the compound useful in numerous synthetic applications.

One of the most important applications of N-Boc-L-alaninol is in pharmaceutical and medicinal chemistry. Chiral amino alcohols are frequently employed as intermediates in the synthesis of drug candidates and biologically active compounds. The stereochemistry present in N-Boc-L-alaninol can be transferred into more complex molecular frameworks, allowing chemists to construct target molecules with controlled three-dimensional structures. Because biological activity often depends strongly on stereochemistry, the availability of enantiomerically pure intermediates such as N-Boc-L-alaninol is of considerable value.

The compound has also been used in the preparation of heterocyclic compounds. Amino alcohol derivatives can undergo a variety of cyclization reactions leading to nitrogen- and oxygen-containing ring systems. Such heterocycles are common structural motifs in pharmaceuticals, agrochemicals, and research compounds. N-Boc-L-alaninol serves as a convenient precursor because its functional groups can be manipulated independently under suitable reaction conditions.

Another documented application is in peptide and peptidomimetic chemistry. Researchers have employed amino alcohol building blocks to introduce structural diversity into peptide-derived molecules. The protected amino group allows incorporation into synthetic sequences, while the alcohol functionality can be transformed into a variety of other groups. This versatility has supported the development of modified peptides and related compounds for biological studies.

N-Boc-L-alaninol has further been utilized in the synthesis of chiral auxiliaries, ligands, and other stereochemically defined intermediates. The presence of a single stereogenic center and readily transformable functional groups makes it a practical starting material for the preparation of more elaborate chiral molecules. Such applications have contributed to broader efforts in asymmetric synthesis, where control of molecular chirality is essential.

The continued importance of N-Boc-L-alaninol reflects the central role of protected amino alcohols in synthetic chemistry. By combining a stable protecting group, a reactive alcohol function, and a naturally derived stereogenic center, the compound provides a reliable platform for the construction of complex organic molecules. Its documented use in pharmaceutical research, heterocycle synthesis, peptide chemistry, and asymmetric synthesis has established N-Boc-L-alaninol as a valuable intermediate in modern chemical science.

References

2022. Amide Synthesis. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-246-00105

2020. Ni-catalyzed direct alcoholysis of N-acylpyrrole-type tertiary amides under mild conditions. Science China Chemistry.
DOI: 10.1007/s11426-019-9665-5

2019. Darolutamide. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0242