2095504-38-2 | potassium {3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexan-1-yl}trifluoroboranuide

Packsize	Purity	Availability	Price	Discounted Price
100mg	97%	2 weeks	$397.00	$278.00
250mg	97%	2 weeks	$625.00	$437.00
500mg	97%	2 weeks	$1,031.00	$722.00
1g	97%	2 weeks	$1,539.00	$1,077.00

Description

• Catalog Number: AZ97739
• Chemical Name: potassium {3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexan-1-yl}trifluoroboranuide
• CAS Number: 2095504-38-2
• Molecular Formula: C10H16BF3KNO2
• Molecular Weight: 289.1440
• MDL Number: MFCD31556357
• SMILES: O=C(N1CC2C(C1)(C2)[B-](F)(F)F)OC(C)(C)C.[K+]

Upstream Synthesis Route

The upstream synthesis route for potassium {3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexan-1-yl}trifluoroboranuide involves the following steps:

1. Start with the preparation of 3-azabicyclo[3.1.0]hexane through a [2+2+1] cycloaddition reaction involving a diazocarbonyl compound and a vinyl ether, typically requiring a transition-metal catalyst for the cyclopropanation step.

2. Next, perform a regioselective functionalization of the azabicyclic structure to introduce a suitable leaving group at the 1-position; this can be achieved through a halogenation (e.g., bromination) reaction.

3. Introduce the tert-butoxycarbonyl (Boc) protecting group on the azabicyclic nitrogen using Boc-anhydride and a base (such as triethylamine) to yield the corresponding Boc-protected azabicyclohexane derivative.

4. Substitute the halide leaving group for a trifluoroborate anion by a nucleophilic replacement reaction, ideally an S_N2 mechanism, to provide the corresponding azabicyclohexyl trifluoroborate salt.

5. Finally, exchange the counterion with potassium to yield the desired potassium salt. This can be conducted by treating the trifluoroborate salt with a potassium ion source such as potassium carbonate or potassium hexafluorophosphate.

Control of reaction conditions, purification at each step, and characterization (e.g., NMR, HRMS, IR) are crucial for the successful synthesis of the desired compound. The Boc protecting group is generally stable under these conditions and protects the nitrogen during the functionalization steps.