1951424-95-5 | (2S,4S)-4-Fluoro-2-(fluoromethyl)pyrrolidine hydrochloride

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$436.00	$305.00
250mg	95%	in stock	$835.00	$584.00

Description

• Catalog Number: AI43628
• Chemical Name: (2S,4S)-4-Fluoro-2-(fluoromethyl)pyrrolidine hydrochloride
• CAS Number: 1951424-95-5
• Molecular Formula: C5H10ClF2N
• Molecular Weight: 157.5894
• MDL Number: MFCD28119072
• SMILES: FC[C@H]1NC[C@H](C1)F.Cl

Computed Properties

• Complexity: 76.8
• Covalently-Bonded Unit Count: 2
• Defined Atom Stereocenter Count: 2
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1

Upstream Synthesis Route

To synthesize (2S,4S)-4-Fluoro-2-(fluoromethyl)pyrrolidine hydrochloride, one must start with the appropriate chiral precursor to ensure stereochemical integrity throughout the synthesis route. Here is a concise retrosynthetic analysis to approach the target molecule:

1. Chiral Pool Synthesis: Begin with a readily available chiral compound such as (S)-pyroglutamic acid as it has the necessary carboxyl and amino functionalities to forge the pyrrolidine ring while preserving the stereochemistry.

2. Reduction of the carboxyl group: The carboxyl group of (S)-pyroglutamic acid would undergo reduction, potentially using lithium aluminum hydride (LAH) to yield an intermediate hydroxy-substituted pyrrolidine.

3. Halogenation: The secondary alcohol would then undergo a halogenation reaction, specifically a fluorination. This could be achieved using diethylaminosulfur trifluoride (DAST) to introduce a fluorine atom, yielding a 4-fluoropyrrolidine compound.

4. Introduction of fluoromethyl group: For the introduction of the fluoromethyl group, a selective deprotonation step could be executed to form an enolate which would then be subjected to electrophilic fluoromethylation using a reagent like fluoroiodomethane or a similar carbon-fluorine bond-forming reagent.

5. Resolution of Stereochemistry: Ensure that during each step, reaction conditions are maintained such that the stereochemistry is preserved. If any step produces a racemic mixture, chiral resolution techniques like crystallization or chromatography would be implemented to isolate the desired (2S,4S) enantiomer.

6. Formation of hydrochloride salt: Finally, the free base form of (2S,4S)-4-Fluoro-2-(fluoromethyl)pyrrolidine would be treated with hydrochloric acid to form the hydrochloride salt.

In practice, each step would require appropriate purification methods to ensure a high purity of the final product. The use of protecting groups may also be necessary to ensure selective reactivity of functional groups during the synthetic pathway. Each reagent and condition must be selected to maintain chiral integrity for successful synthesis of (2S,4S)-4-Fluoro-2-(fluoromethyl)pyrrolidine hydrochloride.