1630815-57-4 | tert-Butyl n-[(3r,4s)-3-fluoropiperidin-4-yl]carbamate

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$218.00	$152.00
250mg	95%	in stock	$359.00	$252.00
500mg	95%	in stock	$502.00	$352.00
1g	95%	in stock	$712.00	$498.00
5g	95%	in stock	$2,111.00	$1,478.00
10g	95%	in stock	$3,510.00	$2,457.00

Description

• Catalog Number: AV15428
• Chemical Name: tert-Butyl n-[(3r,4s)-3-fluoropiperidin-4-yl]carbamate
• CAS Number: 1630815-57-4
• Molecular Formula: C10H19FN2O2
• Molecular Weight: 218.2685
• MDL Number: MFCD18632653
• SMILES: CC(C)(C)OC(=O)NC1CCNCC1F

Upstream Synthesis Route

The upstream synthesis route of tert-Butyl N-[(3R,4S)-3-fluoropiperidin-4-yl]carbamate involves the following steps:

1. **Synthesis of 3R,4S-fluoropiperidine precursor**: The chiral 3-fluoropiperidine scaffold can be constructed via asymmetric synthesis or resolution of racemic mixtures. This might involve starting with a chiral glycidol derivative that can be converted into the corresponding azide, followed by a reduction to yield the amine, and then a ring-closing reaction to form the piperidine ring.

2. **Chiral resolution**: If a racemic mixture is obtained, a chiral resolution step might be necessary to obtain the (3R,4S)-enantiomer. This can be performed through diastereomeric salt formation using a chiral acid or by chiral chromatography.

3. **Protection of amine**: The free amine of the 3R,4S-fluoropiperidine is then protected using a tert-butyloxycarbonyl (Boc) group. The standard approach for this step involves the reaction of the amine with di-tert-butyl dicarbonate (Boc₂O) in the presence of a base like triethylamine (TEA) to form the Boc-protected amine.

4. **Formation of carbamate**: The protected amine can then be reacted with an isocyanate to form the carbamate. However, since specific N-protected isocyanates are less common as commercial reagents, an alternative pathway would include the direct reaction of the Boc-protected amine with phosgene or diphosgene to form the chloroformate, followed by substitution with a suitable nucleophilic amine to yield the target tert-Butyl N-[(3R,4S)-3-fluoropiperidin-4-yl]carbamate.

Each step should be monitored by appropriate analytical methods, such as chiral HPLC, to confirm stereochemistry, purity, and yield. These reactions would also need to be performed under inert atmosphere conditions, especially when handling sensitive reagents like isocyanates or phosgene, and the reaction conditions optimized for scale-up.