The Production Process of (S)-BnCH2-PyBox,(S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine

The production process of (S)-BnCH2-PyBox,(S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine involves a series of chemical reactions that convert raw materials into the desired product.
This process can be broken down into several steps, including the preparation of the starting materials, the reaction steps, and the purification and isolation of the final product.

Preparation of Starting Materials
The production of (S)-BnCH2-PyBox,(S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine involves several starting materials, which must be prepared before the chemical reactions can take place.
The first step in the preparation of these starting materials is to synthesize the analogous material (S)-4-benzylmethyl-2-oxazolin-2-one (BMO).
This can be done by following a similar synthesis route to that of 4-hydroxy-2-oxazoline (HOBO), as described in the literature (Chem.
Eur.
J.
2007, 13, 9408-9410).

Next, the synthesis of (S)-BnCH2-PyBox,(S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine can proceed by following a similar synthesis route to that described in the literature (J.
Am.
Chem.
Soc.
2011, 133, 1222-1225).
The starting material for this synthesis is iodooxacetamide (IBOX), which is treated with formaldehyde, sodium hydroxide, and tetrabutylammonium iodide in the presence of a base catalyst, such as potassium carbonate.
This reaction generates the intermediate N-iodo succinimide, which can then be treated with a Grignard reagent, such as (S)-BnCH2-PyBox,(S)-4-benzylmethyl-2-oxazolin-2-yl)pyridine (PMB-BMO), to form the desired product.

Reaction Steps
The reaction steps involved in the production of (S)-BnCH2-PyBox,(S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine are as follows:

• N-Iodo succinimide synthesis: IBOX + formaldehyde + NaOH + tetrabutylammonium iodide → N-Iodo succinimide
• Grignard reaction: N-Iodo succinimide + (S)-BnCH2-PyBox,(S)-4-benzylmethyl-2-oxazolin-2-yl)pyridine → (S)-BnCH2-PyBox,(S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine

Purification and Isolation of the Final Product
After the reaction is complete, the product can be purified and isolated using standard techniques such as crystallization, column chromatography, or high-performance liquid chromatography (HPLC).
In the case of (S)-BnCH2-PyBox,(S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine, crystallization is typically used to obtain a pure sample for subsequent characterization.

Characterization of the Final Product
Once the final product has been obtained, it can be analyzed to confirm its structure and purity.
This can be done using a variety of techniques, including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (