2097518-76-6 | (2R,7aS)-2-fluorotetrahydro-1H-pyrrolizine-7a(5H)-methanol

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$13.00	$9.00
250mg	98%	in stock	$21.00	$15.00
500mg	98%	in stock	$22.00	$15.00
1g	98%	in stock	$41.00	$29.00
5g	98%	in stock	$115.00	$80.00
10g	98%	in stock	$199.00	$139.00
25g	98%	in stock	$399.00	$279.00
50g	98%	in stock	$742.00	$519.00
100g	95%	in stock	$1,275.00	$893.00

Description

• Catalog Number: BA23190
• Chemical Name: (2R,7aS)-2-fluorotetrahydro-1H-pyrrolizine-7a(5H)-methanol
• CAS Number: 2097518-76-6
• Molecular Formula: C8H14FNO
• Molecular Weight: 159.2013
• MDL Number: MFCD31641130
• SMILES: OC[C@]12CCCN2C[C@@H](C1)F

Upstream Synthesis Route

The upstream synthesis route for (2R,7aS)-2-fluorotetrahydro-1H-pyrrolizine-7a(5H)-methanol would likely involve the following steps:

1. **Starting Material Preparation:**
- The synthesis may start with a pyrrolidine precursor, such as (S)-pyrrolidin-2-one, to introduce the nitrogen-containing ring structure necessary for pyrrolizine formation.

2. **Ring Expansion and Stereochemical Control:**
- Ring expansion can be performed to generate a seven-membered ring, possibly through a cycloaddition or ring-opening/ring-closing metathesis strategy. It is critical to manage the stereochemistry during this step to ensure the 7aS configuration.

3. **Fluorination:**
- The introduction of the fluorine atom can be achieved through nucleophilic fluorination, using sources like Deoxo-Fluor or DAST (diethylaminosulfur trifluoride) ensuring that the 2R stereochemistry is maintained or introduced. This should be done under conditions that do not epimerize the sensitive stereo-centers.

4. **Hydroxymethyl Group Introduction:**
- The hydroxymethyl group at the relevant carbon may be introduced through approaches such as organometallic reagent addition to an aldehyde or ketone precursor, or via hydroboration-oxidation of an alkene precursor followed by an oxidation step.

5. **Cyclization to Form Pyrrolizine Core:**
- Cyclization to create the pyrrolizine ring system could be enabled by an intramolecular cyclization reaction, potentially facilitated by a suitable catalyst. Formation of the pyrrolizine system usually requires a careful setup to ensure the correct ring size and to preserve the previously installed stereochemistry.

6. **Protection and Deprotection Strategies:**
- Protecting group strategies would be employed throughout to ensure the functional groups tolerate the conditions of the synthetic steps and are revealed in the correct sequence. For example, protecting the hydroxyl group during fluorination might be necessary.

7. **Purification and Stereochemical Analysis:**
- The final steps would involve purification, typically through chromatographic methods, and a rigorous stereochemical analysis, such as NMR spectroscopy or chiral HPLC, to confirm the configuration of the product.

8. **Optimization:**
- Depending on the yield and stereoselectivity, each step may be optimized, and alternative reagents may be considered to improve the overall synthesis.

It is essential to note that obtaining the desired stereochemistry in all steps is critical for the successful synthesis of (2R,7aS)-2-fluorotetrahydro-1H-pyrrolizine-7a(5H)-methanol. Additionally, the outlined steps are a generalized approach and might need significant optimization and adaptation to deal with practical challenges faced during the synthesis.