161401-36-1

Basic information

• Product Name: (S)-(-)-1-TRIMETHYLSILYLAMINO-2-METHOXYMETHYLPYRROLIDINE, TECHN., 80
• Synonyms: (S)-(-)-1-TRIMETHYLSILYLAMINO-2-METHOXYMETHYLPYRROLIDINE, TECHN., 80;(S)-(-)-1-Trimethylsilylamino-2-methoxymethylpyrrolidine, techn., 80%;(S)-(-)-1-Trimethylsilylamino-2-methoxymethylpyrrolidine,80%,techn.
• CAS NO: 161401-36-1
• Molecular Formula: C₉H₂₂N₂OSi
• Molecular Weight: 202.372
• Mol File: 161401-36-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: Freezer (-20°C)
• CAS DataBase Reference: (S)-(-)-1-TRIMETHYLSILYLAMINO-2-METHOXYMETHYLPYRROLIDINE, TECHN., 80(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-TRIMETHYLSILYLAMINO-2-METHOXYMETHYLPYRROLIDINE, TECHN., 80(161401-36-1)
• EPA Substance Registry System: (S)-(-)-1-TRIMETHYLSILYLAMINO-2-METHOXYMETHYLPYRROLIDINE, TECHN., 80(161401-36-1)

Safety Data

• Hazardous Substances Data: 161401-36-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to very slightly yellow liquid

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 

Relevant articles and documents

Diastereo- and enantioselective synthesis of α-substituted β-amino acid esters by tandem Michael-addition/α-alkylation with TMS-SAMP as chiral equivalent of ammonia

The hetero Michael-addition of (S)-(-)2-methoxymethyl-1-trimethylsilylaminopyrrolidine (TMS-SAMP) to α,β-unsaturated esters 1, followed by α-alkylation of the intermediate esterenolates with various electrophiles yields α-substituted β-hydrazino esters 3 of anti-configuration in good to excellent diastereomeric excesses (de = 63 - ≥96%). Subsequent reductive N-N bond cleavage leads to β-amino acid esters 4 (R1 = C6H11) in good yields and high diastereo- and enantiomeric purity (de, ee ≥ 96%). The stereochemistry was confirmed by NMR-spectroscopy and X-ray structure analysis.