N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
- CAS NO.:93102-05-7
- Empirical Formula: C13H23NOSi
- Molecular Weight: 237.41
- MDL number: MFCD00674005
- EINECS: 630-326-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-08 14:19:10
What is N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine?
Chemical properties
N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is clear colorless to light yellow liquid
Physical properties
bp 77–80°C/0.5 mmHg.
The Uses of N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is useful reagent in synthesizing N-benzyl substituted pyrrolidines by [3+2] cycloaddition to α,ßunsaturated esters.
The Uses of N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
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.
The Uses of N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
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.
What are the applications of Application
N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine is Reacted in asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines
Preparation
most conveniently prepared by treatment of benzylamine with chloromethyltrimethylsilane followed by formaldehyde and methanol.Access to higher ether homologs is achieved by replacing methanol with the appropriate alcohol. An alternate procedure involves alkylation of lithium N-benzyltrimethylsilymethylamide with methoxymethyl chloride.
Properties of N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
Boiling point: | 76 °C0.3 mm Hg(lit.) |
Density | 0.928 g/mL at 25 °C(lit.) |
refractive index | n |
Flash point: | 151 °F |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | Soluble in chloroform, ethyl acetate. |
form | Liquid |
pka | 7.29±0.50(Predicted) |
Specific Gravity | 0.928 |
color | Clear colorless to light yellow |
Sensitive | Moisture & Light Sensitive |
Hydrolytic Sensitivity | 2: reacts with aqueous acid |
BRN | 4311216 |
CAS DataBase Reference | 93102-05-7(CAS DataBase Reference) |
Safety information for N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine
InChIKey | RPZAAFUKDPKTKP-UHFFFAOYSA-N |
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