477293-60-0 | (2S,4S)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$38.00	$27.00
250mg	95%	in stock	$69.00	$49.00
1g	95%	in stock	$232.00	$162.00
5g	95%	in stock	$718.00	$503.00
10g	95%	in stock	$1,367.00	$957.00
25g	95%	in stock	$3,050.00	$2,135.00

Description

• Catalog Number: AG31905
• Chemical Name: (2S,4S)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate
• CAS Number: 477293-60-0
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.2628
• MDL Number: MFCD20278358
• SMILES: C[C@H]1C[C@@H](CN1C(=O)OC(C)(C)C)O

Computed Properties

• Complexity: 222
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 2
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 2
• XLogP3: 1.1

Upstream Synthesis Route

The synthesis of (2S,4S)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate can be outlined as follows:

1. **Starting Material**: The synthesis might start from commercially available (S)-pyroglutamic acid as the chiral starting material.

2. **Protection of the Carboxylic Group**: The carboxylic acid group of (S)-pyroglutamic acid is protected using tert-butanol in the presence of acid catalysts such as sulfuric acid or using DCC (Dicyclohexylcarbodiimide) to form the tert-butyl ester derivative.

3. **Reduction of the Lactam Ring**: The lactam of protected pyroglutamic ester is then reduced, generally by employing a reducing agent such as LiAlH4 (Lithium aluminium hydride), to afford the corresponding amino alcohol.

4. **Introduction of the Methyl Group**: The next step involves the introduction of the methyl group at the 2-position. This can be achieved via a reductive amination process with formaldehyde in the presence of a reducing agent like NaBH(OAc)3 (Sodium triacetoxyborohydride), ensuring the stereochemistry is preserved.

5. **Formation of the Pyrrolidine Ring**: Cyclization of the amino alcohol to the pyrrolidine ring structure can be done by intramolecular cyclization, typically acid-catalyzed.

6. **Resolution of Diastereomers**: If the previously mentioned steps produce any diastereomeric mixture, chiral resolution can be carried out to isolate the (2S,4S)-isomer.

7. **Oxidation of the Secondary Alcohol**: The secondary alcohol at the 4-position of the pyrrolidine ring can be oxidized to the corresponding ketone with a suitable oxidizing agent, followed by stereoselective reduction (using, for example, L-Selectride for the S configuration) to form the 4-hydroxy group.

8. **Final Purification**: The product is then purified by methods such as recrystallization or column chromatography, yielding (2S,4S)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate.

Keep in mind that reaction conditions and protecting groups will vary depending on the specific chemical transformations. Each step may require optimization to yield the desired stereochemistry and purity.