3197-42-0

Basic information

• Product Name: (S)-(+)-2-Methylpiperidine
• Synonyms: (S)-(+)-2-METHYLPIPERIDINE;(S)-2-METHYL-PIPERIDINE;(S)-(+)-2-METHYLPIPERIDINE,98%;(2S)-2-methylpiperidine;(S)-(+)-2-Methylpiperidine 97%;Piperidine, 2-methyl-,(2S)-
• CAS NO: 3197-42-0
• Molecular Formula: C₆H₁₃N
• Molecular Weight: 99.17
• Product Categories: API intermediates;Piperidines;Chiral Compound;Chiral Building Blocks;Heterocyclic Building Blocks
• Mol File: 3197-42-0.mol
• Article Data: 30

Chemical Properties

• Melting Point: -31.69°C (estimate)
• Boiling Point: 117-121 °C(lit.)
• Flash Point: 16 °C
• Appearance: /
• Density: 0.823 g/mL at 25 °C(lit.)
• Vapor Pressure: 16.4mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• PKA: 10.63±0.10(Predicted)
• CAS DataBase Reference: (S)-(+)-2-Methylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-Methylpiperidine(3197-42-0)
• EPA Substance Registry System: (S)-(+)-2-Methylpiperidine(3197-42-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 3197-42-0(Hazardous Substances Data)

Usage

Uses

(S)-(+)-2-Methylpiperidine has been used in the preparation of (S)-N-(3-(2-pipecolin-1-yl)propyl)phthalimide by reacting with N-(3-bromopropyl)phthalimide. It may also be used as a starting material in the multi-step synthesis of (2S,6S)-(+)-solenopsin A.

InChI:InChI=1/C6H13N/c1-6-4-2-3-5-7-6/h6-7H,2-5H2,1H3/t6-/m0/s1

Upstream product

• 1558-58-3 (6S)-(+)-6-methylpiperidin-2-one 
• 109-05-7 2-Methylpiperidin 
• 119461-42-6 (S)-N-(p-toluenesulfonyl)-4-amino-1-Z-(trimethylsilyl)-1-pentene 
• 153682-03-2 (S)-1-Benzyl-2-methyl-1,2,3,6-tetrahydro-pyridine 
• 173243-20-4 (S)-2-((S)-2-Methyl-piperidin-1-yl)-2-phenyl-ethanol 
• 5261-58-5 methylpentamethylenediamine 
• 1462-92-6 6-methyl-2,3,4,5-tetrahydro-pyridine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 155322-82-0 (3R,5S,8aS)-1-Benzyl-5-methyl-3-phenyl-octahydro-imidazo[1,2-a]pyridine 
• 173173-75-6 (S)-1-((S)-2-Hydroxy-1-phenyl-ethyl)-6-methyl-piperidin-2-one 
• 3128-06-1 5-ketohexanoic acid 
• 170710-79-9 (3S,8aR)-8a-Methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 153681-98-2 N-Benzyl-4-methyl-N-((Z)-(S)-1-methyl-4-trimethylsilanyl-but-3-enyl)-benzenesulfonamide 
• 153682-00-9 Benzyl-((Z)-(S)-1-methyl-4-trimethylsilanyl-but-3-enyl)-trimethylsilanylmethyl-amine 

Downstream Products

• 3197-43-1 (S)-(+)-2-methyl-1-(4-toluenesulfonyl)piperidine 
• 183903-99-3 (+)-(S)-N-tert-butoxycarbonyl-2-methylpiperidine 
• 273410-39-2 (R)-(2-methylpiperidin-1-yl)(phenyl)methanone 
• 1445589-42-3 methyl ((S)-3-methyl-1-((S)-2-(5-(4-(2-((1S,2S)-2-((S)-2-methylpiperidine-1-carbonyl)cyclopentyl)-1H-imidazol-5-yl)-[1,1‘-biphenyl]-4-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-1-oxobutan-2-yl)carbamate 
• 1443245-37-1 methanesulfonic acid 3-[3-tert-butyl-5-(3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-ureido)-pyrazol-1-yl]-benzyl ester 
• 1443245-38-2 1-[5-tert-butyl-2-(3-chloromethyl-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphtalen-1-yl}-urea 

Relevant articles and documents

A Novel (R)-Imine Reductase from Paenibacillus lactis for Asymmetric Reduction of 3 H-Indoles

A novel (R)-imine reductase (PlRIR) from Paenibacillus lactis was heterologously overexpressed in Escherichia coli, purified and characterized. The purified PlRIR exhibited relatively high catalytic efficiency (kcat/Km=1.58 s-1 mm-1) towards 2,3,3-trimethylindolenine. A panel of 3H-indoles and 3H-indole iodides were reduced by PlRIR to yield the corresponding products with good-to-excellent enantioselectivity (66-98 % ee). In addition, PlRIR also possesses good activities toward other types of imines such as pyrroline, tetrahydropyridine, and dihydroisoquinoline, indicating a reasonably broad substrate acceptance. In a 100 mg scale preparative reaction, 100 mm 2,3,3-trimethylindolenine was converted efficiently to afford (R)-2,3,3-trimethylindoline with 96 % ee and 81 % yield.

Synthesis of: N -heterocycles from diamines via H2-driven NADPH recycling in the presence of O2

Herein, we report an enzymatic cascade involving an oxidase, an imine reductase and a hydrogenase for the H2-driven synthesis of N-heterocycles. Variants of putrescine oxidase from Rhodococcus erythropolis with improved activity were identified. Substituted pyrrolidines and piperidines were obtained with up to 97% product formation in a one-pot reaction directly from the corresponding diamine substrates. The formation of up to 93% ee gave insights into the specificity and selectivity of the putrescine oxidase.

Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines

A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g L-1 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee).