623583-08-4 | ((2S,4S)-4-Fluoropyrrolidin-2-yl)methanol HCl

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$89.00	$62.00
250mg	95%	in stock	$93.00	$65.00
500mg	95%	in stock	$160.00	$112.00
1g	95%	in stock	$232.00	$162.00
5g	95%	in stock	$695.00	$486.00

Description

• Catalog Number: AI53887
• Chemical Name: ((2S,4S)-4-Fluoropyrrolidin-2-yl)methanol HCl
• CAS Number: 623583-08-4
• Molecular Formula: C5H11ClFNO
• Molecular Weight: 155.5983
• MDL Number: MFCD12022660
• SMILES: OC[C@@H]1C[C@@H](CN1)F.Cl

Computed Properties

• Complexity: 78.8
• Covalently-Bonded Unit Count: 2
• Defined Atom Stereocenter Count: 2
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 1

Upstream Synthesis Route

The upstream synthesis route of ((2S,4S)-4-fluoropyrrolidin-2-yl)methanol HCl can be delineated as follows:

1. **Start with L-Proline:**
- Utilize L-Proline as a chiral starting material due to its inherent (S)-stereochemistry, which aligns with the desired (2S,4S) configuration of the target molecule.

2. **Protection of the Amino Group:**
- Introduce a protecting group to the amino functionality of L-Proline to prevent undesired reactions during the subsequent steps. Common protecting groups include Boc (tert-butoxycarbonyl) or Cbz (carbobenzyloxy).

3. **Activation of the Carboxylic Acid:**
- Convert the carboxylic acid of the protected L-Proline to a more reactive intermediate like an acid chloride using thionyl chloride (SOCl2) or oxalyl chloride (COCl)2.

4. **Nucleophilic Fluorination:**
- Subject the activated carboxylic derivative to a nucleophilic substitution reaction using a fluoride source, such as KF or AgF, for the introduction of the fluorine atom. This step yields a protected 4-fluoropyrrolidine derivative.

5. **Hydrolysis and Deprotection:**
- Hydrolyze the carboxylic acid derivative to introduce the hydroxyl group, forming a protected 4-fluoropyrrolidin-2-yl methanol.
- Remove the protecting group from the amine under acidic or basic conditions, depending on the protecting group used, yielding the free amine.

6. **Resolution of Stereoisomers (if required):**
- If the reaction conditions do not strictly maintain chirality, a resolution step using chiral resolution agents may be necessary to achieve the pure (2S,4S) isomer.

7. **Salt Formation:**
- React the free amine with hydrochloric acid to form the hydrochloride salt, providing ((2S,4S)-4-fluoropyrrolidin-2-yl)methanol HCl.

It’s worth noting that specific reagents, solvent systems, and reaction conditions must be optimized to ensure the high yield and enantioselectivity of the desired product throughout this synthetic route.