N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

Base Information

• Chemical Name: N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
• CAS No.: 93102-05-7
• Molecular Formula: C13H23NOSi
• Molecular Weight: 237.417
• Hs Code.: 29319090
• Mol file: 93102-05-7.mol

Synonyms:(Benzyl)(methoxymethyl)(trimethylsilanylmethyl)amine;(N-Benzyl-N-methoxymethylamino)methyltrimethylsilane;N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine;N-Benzyl-N-methoxymethyl-N-[(trimethylsilyl)methyl]amine;NSC 601818;[(Methyloxy)methyl](phenylmethyl)[(trimethylsilyl)methyl]amine;

Chemical Property of N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Refractive Index: n20/D 1.492(lit.)
• Boiling Point: 248.7 °C at 760 mmHg
• PKA: 7.29±0.50(Predicted)
• Flash Point: 104.2 °C
• PSA: 12.47000
• Density: 0.934 g/cm³
• LogP: 3.38820
• Storage Temp.: Refrigerator
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Soluble in chloroform, ethyl acetate.

Purity/Quality:

99% ^*data from raw suppliers

N-(Methoxymethyl)-N-[(trimethylsilyl)methyl]benzenemethanamine(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Physical properties: bp 77–80°C/0.5 mmHg.
• Uses: N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is useful reagent in synthesizing N-benzyl substituted pyrrolidines by [3+2] cycloaddition to α,?unsaturated esters. N-Benzyl-N-(methoxymethyl)- N-trimethylsilylmethylamine (1) is a valuable reagent for in situ generation of the N-benzyl azomethine ylide (2). It is generally preferred over alternative silylmethylamine precursors6–8 because of ease of handling and use. The ylide (2) is most conveniently generated from (1) using a catalytic amount of trifluoroacetic acid as described by Achiwa.Alternative catalysts include LiF, TBAF,Me3SiOTf–CsF, or Me3SiI–CsF. Mechanistic studies provide evidence that the reactive intermediate generated from (1) with either CF3CO2H or F? is a 1,3-dipolar species. Reaction of (2) with alkenes provides an efficient convergent route to pyrrolidine derivatives. Alkynes afford 3-pyrrolines which can be converted into pyrroles.The ylide (2) reacts most readily with electron deficient alkenes and alkynes since this pairing results in a narrow dipole HOMO–dipolarophile LUMO energy gap.Examples of suitable dipolarophiles include unsaturated esters, ketones, imides,nitriles,and sulfones. Cycloaddition occurs with complete cis stereospecificity (eq 1) which is consistent with a concerted mechanism. Dipolarophiles containing an endocyclic double bond afford fused bicyclic pyrrolidines, whereas substrates with an exocyclic double bond provide access to spirocyclic systems. N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine forms azomethine ylides which readily undergo [3+2] cycloaddition to α,?-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields. It reacts with asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines. It is used in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds.

Technology Process of N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine

There total 12 articles about N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine 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: 97.5%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-(trimethylsilylmethyl)benzylamine (53215-95-5) → N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7)

Guidance literature:

formaldehyd; N-(trimethylsilylmethyl)benzylamine; In water; at 0 ℃;

With potassium carbonate; In water; at 20 ℃; for 2h;

Reference yield: 94.0%

methanol (67-56-1) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + N-(trimethylsilylmethyl)benzylamine (53215-95-5) → N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7)

Guidance literature:

DOI:10.1016/j.bmcl.2009.09.044

Reference yield: 90.0%

N-(trimethylsilylmethyl)benzylamine (53215-95-5) + chloromethyl methyl ether (107-30-2) → N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -70 deg C; 2.) 3 h, -70 deg C;

upstream raw materials:

methanol

formaldehyd

N-(trimethylsilylmethyl)benzylamine

chloromethyl methyl ether

Downstream raw materials:

(1R*,5S*)-N-benzyl-3-azabicyclo<3.3.0>octan-8-one

N-[(Benzyl-trimethylsilanylmethyl-amino)-methyl]-thioacetamide

(S)-3-((3S,4S)-1-Benzyl-4-cyclopropyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one

(S)-3-((3R,4R)-1-Benzyl-4-cyclopropyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one

Refernces

• 1、 Buev, Evgeny M.,Stepanov, Maxim A.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.. "Synthesis of 6,12-Methanodibenzo[ c, f]azocines and 4-Aryltetrahydroisoquinolines from Aromatic Aldehydes". supporting information. p. 631 - 635. Retrieved 2020/01/31.
• 2、 -. "A fluorine-containing substituted benzimidazole derivative and application thereof (by machine translation)". Paragraph 0117; 0118; 0119. . Retrieved 2019/01/08.