N-Boc-pyrroline

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Cat Number

INT73286701

CAS Number

73286-70-1

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Product Detail Description Scientific Support Customer Q&A

CAS Number

73286-70-1

Synonyms

1-tert-Butoxycarbonylpyrroline;2,5-Dihydro-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester

Molecular Formula

C9H15NO2

Molecular Weight

169.22

Smiles

N1(C(OC(C)(C)C)=O)CC=CC1

Melting Point

40℃

Boiling Point

208℃

Relative Density

0.98

General Description

N-Boc-pyrroline (1-Boc-2,5-dihydro-1H-pyrrole) is a protected unsaturated five-membered nitrogen heterocycle (pyrroline) bearing a tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom. The N-Boc protection renders the nitrogen non-nucleophilic and base-stable, while the C=C double bond in the ring provides a site for further chemical elaboration through cycloaddition, hydrogenation, or olefin metathesis reactions.

Mechanism of Action

N-Boc-pyrroline functions as a protected heterocyclic building block in the synthesis of pyrrolidine-containing pharmaceuticals and natural products. The N-Boc group is orthogonally stable to a range of reaction conditions (acidic conditions specifically cleave it) and can be removed under mild acidic conditions (e.g., TFA in DCM) at a late synthetic stage. The double bond allows for further functionalization including dihydroxylation, epoxidation, and cycloaddition reactions to introduce additional stereocenters.

Application

N-Boc-pyrroline is used as a versatile protected heterocyclic building block in the synthesis of pharmaceutical intermediates, particularly those targeting the CNS, where the pyrrolidine and pyrroline cores are prevalent in receptor ligands and neurotransmitter analogs. It is used in the synthesis of GABAergic compounds, NMDA receptor modulators, and sigma receptor ligands. The Boc-protected form is preferred for multi-step synthesis due to its stability and ease of removal.

Asymmetric hydroformylation of N-Boc-2-pyrroline and N-Boc-3-pyrroline was achieved using a rhodium catalyst with bisphosphine ligand 1c. The reaction of N-Boc-2-pyrroline at 60°C under 20 bar syngas (CO/H₂ = 15:5) gave the chiral aldehyde product in 96% enantioselectivity with full conversion. N-Boc-3-pyrroline afforded 92% ee under the same catalytic system, producing exclusively one regioisomer. These chiral aldehydes can be oxidized to enantioenriched β-proline in two steps, which is a key structural element for peptide and protein synthesis. The products also serve as intermediates for MCH-R1 antagonist, an anti-obesity agent. The bisphosphine ligand with ortho-chloride substituents provided the highest enantioselectivity among tested ligands.

Fig. 1 Conversion of AHF of N-Boc pyrroline into b-proline. (Zheng X.; et al. 2015)

References

Zheng X, et al. Highly selective bisphosphine ligands for asymmetric hydroformylation of heterocyclic olefins. Tetrahedron Letters, 2015, 56(9): 1149-1152.

What is the recommended storage condition for N-Boc-pyrroline?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for N-Boc-pyrroline?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

What is the primary synthetic application of N-Boc-pyrroline?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

What analytical characterization data is available for N-Boc-pyrroline?

Standard analytical data including HPLC purity profile, NMR confirmation, and physical specifications are included in the COA. Additional characterization data can be arranged upon request.

Is N-Boc-pyrroline manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.