114676-93-6 | (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$203.00	$142.00
1g	95%	in stock	$480.00	$336.00
5g	95%	in stock	$1,549.00	$1,084.00

Description

• Catalog Number: AA19269
• Chemical Name: (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine
• CAS Number: 114676-93-6
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.2628
• MDL Number: MFCD11975977
• SMILES: C[C@@H]1C[C@H](CN1C(=O)OC(C)(C)C)O

Upstream Synthesis Route

The upstream synthesis of (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine typically involves the following steps:

1. **Starting Material:** The synthesis commonly starts with (R)-2-methyl-4-hydroxypentanoic acid as the chiral starting material.

2. **Cyclization:** The carboxylic acid is converted to an amide using ammonia or an amine derivative, followed by cyclization to form the pyrrolidine ring. Cyclization can be achieved through intramolecular amidation using dehydration agents like dicyclohexylcarbodiimide (DCC) or by using amine sources like azides and reducing them afterward.

3. **Chiral Resolution:** If the starting material is not enantiomerically pure, chiral resolution may be necessary to obtain the (2R,4R)-enantiomer.

4. **Hydroxy Group Protection:** The hydroxy group at the 4-position is protected as a tert-butyloxycarbonyl (Boc) group using di-tert-butyl dicarbonate (Boc_2O) in the presence of a base like triethylamine (Et_3N).

5. **Purification and Isolation:** The final product is purified, typically through chromatography, and isolated as a pure enantiomer.

Each step needs to be carefully controlled to preserve stereochemistry and achieve high purity and yield. Analytical techniques such as chiral HPLC are used throughout the process to monitor the stereochemical outcomes and purity of the intermediates and final product.