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

Downstream Products

• 3197-42-0 (S)-2-methylpiperidine 
• 6879-74-9 himbacine 
• 518-99-0 himbeline 
• 6879-73-8 Himandravine 
• 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 
• 183747-92-4 1,1-dimethyl<(2R,6S)-2-<(1E,3Z,5S)-5-hydroxy-1,3-hexadienyl>-6-methyl-1-piperidine>carboxylate 

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

Asymmetrie substitutions of 2-lithiated N-boc-piperidine and N-boc-azepine by dynamic resolution

Proton abstraction of N-tertbutoxycarbonyl-piperidine (N-Boc-piperidine) with sBuLi and TMEDA provides a racemic organolithium that can be resolved using a chiral ligand. The enantiomeric organolithiums can interconvert so that a dynamic resolution occurs. Two mechanisms for promoting enantioselectivity in the products are possible. Slow addition of an electrophile such as trimethylsilyl chloride allows dynamic resolution under kinetic control (DKR). This process occurs with high enantioselectivity and is successful by catalysis with substoichiometric chiral ligand (catalytic dynamic kinetic resolution). Alternatively, the two enantiomers of this organolithium can be resolved under thermodynamic control with good enantioselectivity (dynamic thermodynamic resolution, DTR). The best ligands found are based on chiral diamino-alkoxides. Using DTR, a variety of electrophiles can be used to provide an asymmetric synthesis of enantiomerically enriched 2-substituted piperidines, including (after Boc deprotection) the alkaloid (+)-ss-conhydrine. The chemistry was extended, albeit with lower yields, to the corresponding 2-substituted sevenmembered azepine ring derivatives.

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