183903-99-3

Basic information

• Product Name: (S)-(+)-N-TBOC-2-METHYLPIPERIDINE
• Synonyms: (S)-(+)-N-TBOC-2-METHYLPIPERIDINE;(S)-(+)-N-TERT-(BUTOXYCARBONYL)-2-METHYLPIPERIDINE;S-(+)-N-TERT-(BUTOXYCARBONYL);(S)-(+)-N-(Boc)-2-Methylpiperidine
• CAS NO: 183903-99-3
• Molecular Formula: C₁₁H₂₁NO₂
• Molecular Weight: 199.29
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Piperidines
• Mol File: 183903-99-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 54-56 °C0.05 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: /
• Density: 0.937 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0167mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• CAS DataBase Reference: (S)-(+)-N-TBOC-2-METHYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-N-TBOC-2-METHYLPIPERIDINE(183903-99-3)
• EPA Substance Registry System: (S)-(+)-N-TBOC-2-METHYLPIPERIDINE(183903-99-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 183903-99-3(Hazardous Substances Data)

Usage

General Description

(S)-(+)-N-TBOC-2-METHYLPIPERIDINE is a chemical compound with the molecular formula C16H25NO4. It is a chiral auxiliary commonly used in organic synthesis for the preparation of enantiomerically pure compounds. (S)-(+)-N-TBOC-2-METHYLPIPERIDINE is often employed as a reagent in asymmetric synthesis to control the stereochemistry of chemical reactions. It is also used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other biologically active compounds. Additionally, (S)-(+)-N-TBOC-2-METHYLPIPERIDINE has applications in the field of medicinal chemistry and drug discovery. Due to its versatile nature and chiral properties, this compound plays a crucial role in the synthesis of complex molecules with specific stereochemical properties.

InChI:InChI=1/C11H21NO2/c1-9-7-5-6-8-12(9)10(13)14-11(2,3)4/h9H,5-8H2,1-4H3/t9-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 36702-48-4 (S)-2-methyl-piperidine; L_g-hydrogentartrate 
• 3197-42-0 (S)-2-methylpiperidine 
• 75-77-4 chloro-trimethyl-silane 
• 75844-69-8 t-butyl piperidinecarboxylate 
• 77-78-1 dimethyl sulfate 
• 123387-55-3 1-t-butoxycarbonyl-2-tributylstannylpiperidine 
• 74-88-4 methyl iodide 
• 321885-26-1 (S)-6-Methyl-1-((R)-1-phenyl-ethyl)-piperidin-2-one 
• 321885-24-9 N-isopropenyl-N-(1-phenyl-ethyl)-acrylamide 
• 109-05-7 2-Methylpiperidin 
• 321885-28-3 (S)-2-Methyl-1-[(R)-1-phenylethyl]piperidine 

Downstream Products

• 183747-92-4 1,1-dimethyl<(2R,6S)-2-<(1E,3Z,5S)-5-hydroxy-1,3-hexadienyl>-6-methyl-1-piperidine>carboxylate 
• 344335-56-4 (2S,6S)-2-[(1E,3Z)-(S)-5-((E)-3-Cyclohex-1-enyl-acryloyloxy)-hexa-1,3-dienyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester 
• 6879-73-8 Himandravine 
• 518-99-0 himbeline 
• 6879-74-9 himbacine 
• 3197-42-0 (S)-2-methylpiperidine 

Relevant articles and documents

Biomimetic approach to Galbulimina type I alkaloids

On treatment with trifluoroacetic acid the tetraene precursor 23 underwent Boc deprotection, condensation and an iminium ion accelerated intramolecular Diels-Alder cycloaddition resulting in an iminium species 12, which was further converted into himbacin

Biomimetic total synthesis of (+)-himbacine

(Chemical Equation Presented) On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensation followed by an iminium ion activated intramolecular Diels-Alder cycloaddition to give the (+)-himbacine precursor 11 on reduct

Asymmetric deprotonation of N -boc piperidine: React IR monitoring and mechanistic aspects

The high yielding asymmetric deprotonation trapping of N-Boc piperidine is successfully realized using s-BuLi and a (+)-sparteine surrogate. Monitoring of the lithiation by in situ React IR allowed the direct observation of a prelithiation complex.

Dynamic kinetic and kinetic resolution of N-Boc-2-lithiopiperidine

Asymmetric substitution of 2-lithiopiperidines can be achieved by dynamic resolution; the organolithium is formed as a racemic mixture by proton abstraction (or tin-lithium exchange) and is resolved in the presence of a chiral ligand. The Royal Society of