(3S,4S)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one

Base Information

• Chemical Name: (3S,4S)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one
• CAS No.: 132695-96-6
• Molecular Formula: C₅H₁₀N₂O₂
• Molecular Weight: 130.147
• DSSTox Substance ID: DTXSID00157720
• Wikidata: Q83025874
• ChEMBL ID: CHEMBL165945
• Mol file: 132695-96-6.mol

Synonyms:cis-4-methyl-HA-966;L 687,414;L 687414;L 687414, (3R-cis)-isomer;L-687,414;L-687414

Chemical Property of (3S,4S)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one

Chemical Property:

• Vapor Pressure: 0.00277mmHg at 25°C
• Boiling Point: 253.7°Cat760mmHg
• Flash Point: 107.3°C
• PSA: 66.56000
• Density: 1.29g/cm³
• LogP: -0.18060
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.074227566
• Heavy Atom Count: 9
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(C(=O)C1N)O
• Isomeric SMILES: C[C@H]1CN(C(=O)[C@H]1N)O

Technology Process of (3S,4S)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one

There total 31 articles about (3S,4S)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(3S,4S) 1-benzyloxy-4-methyl-3-<(R)-1-phenylethylamino>-2-pyrrolidinone (130865-77-9) → 3S-amino-1-hydroxy-4S-methylpyrrolidin-2-one (132695-96-6)

Guidance literature:

With hydrogen; acetic acid; palladium dihydroxide; In methanol; for 2h; under 2585.7 Torr;

DOI:10.1016/S0040-4020(01)88493-3

Reference yield:

ethyl 3-formylbutyrate (54998-57-1) → cis-3-amino-1-hydroxy-4-methylpyrrolidin-2-one (130865-65-5,130931-65-6,132619-43-3,132619-44-4,132695-96-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N

2: NaCNBH₃, HCl

3: NaOMe / methanol

4: KN(SiMe₃)2 / tetrahydrofuran / -100 °C

5: CF₃CO₂H

6: H₂ / Pd/C

7: H₂ / Pt

With hydrogenchloride; hydrogen; sodium methylate; potassium hexamethylsilazane; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; platinum; In tetrahydrofuran; methanol;

DOI:10.1039/c39900001578

Reference yield:

ethyl 3-formylbutyrate (54998-57-1) → trans-3-amino-1-hydroxy-4-methylpyrrolidin-2-one (130865-65-5,130931-65-6,132619-43-3,132619-44-4,132695-96-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N

2: NaCNBH₃, HCl

3: NaOMe / methanol

4: KN(SiMe₃)2 / tetrahydrofuran / -100 °C

5: CF₃CO₂H

6: H₂ / Pd/C

7: H₂ / Pt

With hydrogenchloride; hydrogen; sodium methylate; potassium hexamethylsilazane; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; platinum; In tetrahydrofuran; methanol;

DOI:10.1039/c39900001578

upstream raw materials:

(3S,4S) 1-benzyloxy-4-methyl-3-<(R)-1-phenylethylamino>-2-pyrrolidinone

1-benzyloxy-4-methylpyrrolidin-2-one

1-benzyloxy-3-hydroxy-4-methyl-2-pyrrolidinone

1-benzyloxy-4-methyl-pyrrolidine-2,2-dione

Refernces

Design, synthesis and structure-activity relationships of novel strychnine-insensitive glycine receptor ligands

10.1016/S0960-894X(99)00194-8

The research aimed to design, synthesize, and investigate the structure-activity relationships of novel ligands that act at the strychnine-insensitive glycine site of the NMDA receptor. This site is of interest due to its potential therapeutic relevance in various disorders, including cognitive deficits, epilepsy, schizophrenia, pain, depression, and stroke. The study focused on 3-hydroxy-imidazolidin-4-one derivatives, using D-cycloserine (DCS) and L-687,414 as templates due to their rigid framework and spatial orientation of pharmacophores. The researchers synthesized a series of compounds and evaluated their affinities and efficacies at the target site. The most active compound, 3a, exhibited affinity and efficacy similar to DCS, a known partial agonist. However, modifications to the structure of 3a, such as the addition of methyl or hydroxymethyl groups, expansion of the ring size, or replacement of the basic nitrogen with a sulfur atom, generally led to a loss of activity.

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