137496-71-0

Basic information

• Product Name: (S)-1-BOC-2-METHYLPYRROLIDINE
• Synonyms: (S)-1-BOC-2-METHYLPYRROLIDINE;(S)-N-Boc-2-methylpyrrolidine;(S)-2-Methyl-pyrrolidine-1-carboxylic acid tert-butyl ester;Zinc04203908;(S)-tert-Butyl 2-Methylpyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid, 2-Methyl-, 1,1-diMethylethyl ester, (2S)-
• CAS NO: 137496-71-0
• Molecular Formula: C₁₀H₁₉NO₂
• Molecular Weight: 185.26
• Product Categories: Heterocyclic Compounds
• Mol File: 137496-71-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 233.962 °C at 760 mmHg
• Flash Point: 82 °C
• Appearance: /
• Density: 0.962 g/mL at 25 °C
• Vapor Pressure: 0.054mmHg at 25°C
• Refractive Index: n20/D 1.444
• Storage Temp.: 2-8°C
• PKA: -1.21±0.40(Predicted)
• CAS DataBase Reference: (S)-1-BOC-2-METHYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-BOC-2-METHYLPYRROLIDINE(137496-71-0)
• EPA Substance Registry System: (S)-1-BOC-2-METHYLPYRROLIDINE(137496-71-0)

Safety Data

• Hazard Codes: T,N
• Statements: 25-37/38-41-50
• Safety Statements: 26-39-45-61
• RIDADR: UN 2810 6.1/PG 3
• Hazardous Substances Data: 137496-71-0(Hazardous Substances Data)

Usage

General Description

"(S)-1-Boc-2-methylpyrrolidine" is a type of chemical compound that belongs to the group of pyrrolidines. Pyrrolidines are organic compounds primarily found in the alkaloids of many plants and are often used in organic chemistry as a synthetic building block. This particular compound, being chiral, can be used in the creation of asymmetric organic molecules - critical for a variety of pharmaceutical applications. It is generally stable, thought it may be sensitive to moisture. The compound can be stored at room temperature but should be protected from the light. It’s dangerous if it comes into contact with the skin or eyes and if swallowed or inhaled. Appropriate protective measures including gloves, lab-coats, and safety goggles should be used when handling this chemical.

InChI:InChI=1/C10H19NO2/c1-8-6-5-7-11(8)9(12)13-10(2,3)4/h8H,5-7H2,1-4H3/t8-/m0/s1

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 77-78-1 dimethyl sulfate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 74-88-4 methyl iodide 
• 128510-88-3 tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate 
• 132482-10-1 (R)-1-<(1,1-dimethylethoxy)carbonyl>-2-pyrrolidinemethanolmethanesulfonate 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 765-38-8 (S)-2-methylpyrrolidine 

Downstream Products

• 765-38-8 (S)-2-methylpyrrolidine 
• 1212353-38-2 (S)-2-methylpyrrolidine 4-methylbenzenesulfonic acid 
• 92012-42-5 (2S,5R)-2,5-Dimethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 156038-84-5 (2S,5S)-2,5-Dimethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

The Configuration Stability of Chiral Lithio α-Amino Carbanions. The Effect of Li-O vs. Li-N Complexation.

α-Lithio pyrrolidine, as its N-t-BOC or formamidine derivative, has been generated in high enantiomeric purity via Sn-Li exchange of the enantiomerically enriched (88-95percent) α-tributylstannane derivative, 4.The alkylation of these lithio carbanions gave 2-methyl pyrrolidines as well as providing a measure of their configurational stability.It was found that the α-lithio formamidines were configurationally more stable than the t-BOC derivatives and this is attributed to, the stronger O-Li bond which weakens the adjacent C-Li bond, thus allowing configurational decay to occur more readily.This is the first report wherein a difference is observed between O-Li-C and N-Li-C configurational stability.

Asymmetric lithiation trapping of N -boc heterocycles at temperatures above -78°C

The asymmetric lithiation trapping of N-Boc heterocycles using s-BuLi/chiral diamines at temperatures up to -20°C is reported. Depending on the N-Boc heterocycle, lithiation is accomplished using s-BuLi and (-)-sparteine or the (+)-sparteine surrogate in the temperature range -50 to -20°C for short reaction times (2-20 min). Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered functionalized N-Boc heterocycles in 47-95% yield and 77:23-93:7 er. With N-Boc pyrrolidine, trapped products can be generated in ～90:10 er even at -20°C.

LXR AND FXR MODULATORS

Compounds of the invention are disclosed, such as compounds of formulae LX - LXIV, and pharmaceutically acceptable salts, isomers, or prodrugs thereof, which are useful as modulators of the activity of liver X receptors (LXR) and Farnesoid X receptors (FXR), where R00, R200, R400, R500, J11, J21, G1, G21, and Q are defined herein. Pharmaceutical compositions containing the compounds and methods of using the compounds are also disclosed.