317356-27-7 | (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoro-2-hydroxymethylpyrrolidine

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$90.00	$63.00
1g	97%	in stock	$251.00	$176.00
5g	97%	in stock	$713.00	$499.00
10g	97%	in stock	$1,179.00	$825.00
25g	97%	in stock	$2,112.00	$1,479.00

Description

• Catalog Number: AF87545
• Chemical Name: (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoro-2-hydroxymethylpyrrolidine
• CAS Number: 317356-27-7
• Molecular Formula: C10H18FNO3
• Molecular Weight: 219.2532
• MDL Number: MFCD19440847
• SMILES: OC[C@@H]1C[C@@H](CN1C(=O)OC(C)(C)C)F

Computed Properties

• Complexity: 239
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 2
• Heavy Atom Count: 15
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 3
• XLogP3: 1

Upstream Synthesis Route

The upstream synthesis route of (2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoro-2-hydroxymethylpyrrolidine can be accomplished through the following steps:

1. **Enantioselective Synthesis of Pyrrolidine Core**: Begin with asymmetric synthesis to construct the pyrrolidine ring with the desired stereochemistry (S,S). This could involve starting with a prochiral succinimide, derivative or glutaric acid, and employing chiral auxiliaries or catalysts for enantioselective cyclization.

2. **Functionalization at C-4**: Introduce a fluoro substituent at the C-4 position. This could be achieved using nucleophilic fluorination agents such as Deoxo-Fluor or DAST (Diethylaminosulfur Trifluoride) where the pre-existing functional group at the 4-position can be substituted by fluorine.

3. **Introduction of Hydroxymethyl Group**: Perform a regioselective alkylation at C-2 to insert the hydroxymethyl group. Utilize a reagent like formaldehyde for a direct hydroxymethylation or a protected form of it, followed by deprotection if necessary.

4. **Protection of Amine and Hydroxyl Groups**: Protect the amine group by Boc (tert-Butyloxycarbonyl) using di-tert-butyl dicarbonate (Boc₂O) in the presence of a base. The hydroxyl group can remain unprotected, or if required, be protected temporarily during the amine protection step and later deprotected.

5. **Purification and Characterization**: Finally, purify the target compound using appropriate chromatographic techniques and characterize it via NMR, IR, and mass spectrometry to ensure structural and stereochemical integrity of the product.

Each of these steps should be followed by intermediates with thorough purification and characterization to ensure the stereochemistry and structural integrity of the molecule is preserved throughout the synthesis. This is a general synthetic outline and actual reagents and conditions may vary depending on specific reaction optimizations and substrate scope.