(R)-(-)-N-Boc-3-pyrrolidinol
[CAS 109431-87-0]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (R)-(-)-N-Boc-3-pyrrolidinol
• Synonyms: N-tert-Butoxycarbonyl-(R)-(-)-3-pyrrolidinol
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.24
• CAS Registry Number: 109431-87-0
• EC Number: 629-335-6
• SMILES: CC(C)(C)OC(=O)N1CC[C@H](C1)O

Properties

• Melting point: 62-65 °C
• alpha: -7 ° (c=1, MeOH)

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H400
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

(R)-(-)-N-Boc-3-pyrrolidinol is a chiral amine that has garnered attention in the field of organic synthesis and medicinal chemistry due to its versatile reactivity and role as a key building block in the synthesis of various pharmaceuticals. The compound is characterized by its Boc (tert-butyloxycarbonyl) protecting group, which enhances its stability and reactivity in synthetic pathways.

The discovery of (R)-(-)-N-Boc-3-pyrrolidinol can be linked to the development of methods for synthesizing chiral amines, which are crucial in the pharmaceutical industry for producing biologically active compounds. The importance of chirality in drug development has driven researchers to explore various synthetic routes for obtaining enantiomerically pure substances. The synthesis of (R)-(-)-N-Boc-3-pyrrolidinol typically involves the resolution of racemic mixtures or asymmetric synthesis methods. The development of this compound has facilitated the advancement of more efficient synthetic strategies in organic chemistry.

In terms of applications, (R)-(-)-N-Boc-3-pyrrolidinol serves as a versatile intermediate in the synthesis of several pharmaceutical agents, including those targeting central nervous system disorders and other therapeutic areas. Its functionality allows for further transformations, such as the introduction of various functional groups, which can modify biological activity and enhance the pharmacokinetic properties of the resulting compounds.

Additionally, (R)-(-)-N-Boc-3-pyrrolidinol is employed in the preparation of more complex structures through coupling reactions, enabling the formation of peptide bonds or the synthesis of heterocyclic compounds. Its utility in drug discovery and development has made it an essential component in the arsenal of synthetic chemists.

Research into the properties and applications of (R)-(-)-N-Boc-3-pyrrolidinol continues to evolve, with ongoing studies aimed at improving synthetic methodologies and expanding its use in various therapeutic contexts. The compound's role as a chiral building block exemplifies the critical intersection of chemistry and pharmacology in modern drug development.

References

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DOI: 10.1007/s10529-016-2167-3

2009. A Practical Synthesis of Differentially Protected 4,4'-Dipiperidinyl Ethers: Novel Ligands of Pharmaceutical Interest. Synlett.
DOI: 10.1055/s-0028-1088154

2007. Engineering the phenylacetaldehyde reductase mutant for improved substrate conversion in the presence of concentrated 2-propanol. Applied Microbiology and Biotechnology.
DOI: 10.1007/s00253-007-1223-2