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Safety Information

391204

Sigma-Aldrich

Methyl pipecolinate hydrochloride

97%

Synonym(s):

Methyl 2-piperidinecarboxylate hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C7H13NO2 · HCl
CAS Number:
32559-18-5
Molecular Weight:
179.64
MDL number:
MFCD00192316
UNSPSC Code:
12352100
PubChem Substance ID:
24864365
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

205 °C (dec.) (lit.)

SMILES string

Cl.COC(=O)C1CCCCN1

InChI

1S/C7H13NO2.ClH/c1-10-7(9)6-4-2-3-5-8-6;/h6,8H,2-5H2,1H3;1H

InChI key

APCHKWZTSCBBJX-UHFFFAOYSA-N

General description

Methyl pipecolinate hydrochloride is a hydrochloride salt of methyl piperidine-2-carboxylate (methyl pipecolinate). The kinetics of the enzymatic separation of enantiomeric forms of methyl pipecolinate using Candida antarctica Lipase A (CAL-A) has been reported. Its role as catalyst for the standard Diels-Alder reaction has been examined.

Application

Reactant for synthesis of:
A pipecolic linker
Antiviral agents
Aurora and epidermal growth factor receptor kinase inhibitor
Pyrrolidine derivatives via reduction of substituted pyrroles

Reactant for:
Petasis reactions
Decarbonylative radical cyclization of alpha-amino selenoesters upon electrophilic alkenes

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

391204-VAR:
391204-BULK:
391204-5G:
391204-25G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Advances in the kinetic and dynamic kinetic resolution of piperazine-2-carboxylic acid derivatives with Candida antarctica lipase A; structural requirements for enantioselective N-acylation.
Hietanen A, et al.
ARKIVOC (Gainesville, FL, United States), 5, 60-74 (2012)
Aldehyde-based racemization in the dynamic kinetic resolution of N-heterocyclic a-amino esters using Candida Antarctica lipase A.
Liljeblad A, et al.
Tetrahedron, 60(3), 671-677 (2004)
The α-effect in cyclic secondary amines: new scaffolds for iminium ion accelerated transformations.
Brazier JB, et al.
Tetrahedron, 65(48), 9961-9966 (2009)
Enantioselective lipase-catalyzed reactions of methyl pipecolinate: transesterification and N-acylation.
Liljeblad, A, et al.
Tetrahedron Letters, 43(13), 2471-2474 (2002)
Alkoxycarbonylpiperidines as N-nucleophiles in the palladium-catalyzed aminocarbonylation.
Takacs A, et al.
Monatshefte fur Chemie / Chemical Monthly, 145(9), 1473-1478 (2014)

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