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(S)-2-(Aminomethyl)-1-Cbz-pyrrolidine, also known as (S)-Benzyl 2-(aminomethyl)pyrrolidine-1-carboxylate, is an organic compound with a molecular structure that features a pyrrolidine ring, an aminomethyl group, and a carbamate protecting group. It is a chiral molecule with a specific (S)-configuration, which is crucial for its reactivity and applications in various chemical and pharmaceutical processes.

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  • 119020-03-0 Structure
  • Basic information

    1. Product Name: (S)-2-(Aminomethyl)-1-Cbz-pyrrolidine
    2. Synonyms: 2-AMINOMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER;(+/-)-2-(AMINOMETHYL)-1-N-CBZ-PYYROLIDINE;1-N-CBZ-2-(AMINOMETHYL)PYRROLIDINE;1-CBZ-2-AMINOMETHYL PYRROLIDINE;4-AMINOMETHYL-1-N-CBZ-PIPERIDINE;4-AMINOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID BENZYL ESTER;4-(AMINOMETHYL)PIPERIDINE, N-CBZ PROTECTED;BUTTPARK 93\50-51
    3. CAS NO:119020-03-0
    4. Molecular Formula: C13H18N2O2
    5. Molecular Weight: 234.29
    6. EINECS: N/A
    7. Product Categories: Pyrrole&Pyrrolidine&Pyrroline
    8. Mol File: 119020-03-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 370.5 °C at 760 mmHg
    3. Flash Point: 177.9 °C
    4. Appearance: /
    5. Density: 1.155 g/cm3
    6. Vapor Pressure: 1.1E-05mmHg at 25°C
    7. Refractive Index: 1.56
    8. Storage Temp.: Room temperature.
    9. Solubility: N/A
    10. PKA: 9.91±0.29(Predicted)
    11. CAS DataBase Reference: (S)-2-(Aminomethyl)-1-Cbz-pyrrolidine(CAS DataBase Reference)
    12. NIST Chemistry Reference: (S)-2-(Aminomethyl)-1-Cbz-pyrrolidine(119020-03-0)
    13. EPA Substance Registry System: (S)-2-(Aminomethyl)-1-Cbz-pyrrolidine(119020-03-0)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 36/37/38-41-37/38-22
    3. Safety Statements: 26-36/37/39-39
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 119020-03-0(Hazardous Substances Data)

119020-03-0 Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-(Aminomethyl)-1-Cbz-pyrrolidine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for the development of new drugs, particularly those targeting the central nervous system.
Used in Chemical Synthesis:
(S)-2-(Aminomethyl)-1-Cbz-pyrrolidine is used as a reagent in the preparation of specific chemical compounds, such as trifluoro-N-[(S)-pyrrolidinylmethyl]methanesulfonamide. Its chiral nature and functional groups allow for selective reactions and the formation of complex molecules with potential applications in various fields.

Check Digit Verification of cas no

The CAS Registry Mumber 119020-03-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,0,2 and 0 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 119020-03:
(8*1)+(7*1)+(6*9)+(5*0)+(4*2)+(3*0)+(2*0)+(1*3)=80
80 % 10 = 0
So 119020-03-0 is a valid CAS Registry Number.
InChI:InChI=1/C13H18N2O2/c14-9-12-7-4-8-15(12)13(16)17-10-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-10,14H2

119020-03-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-2-(Aminomethyl)-1-Cbz-Pyrrolidine

1.2 Other means of identification

Product number -
Other names Benzyl 2-(aminomethyl)pyrrolidine-1-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:119020-03-0 SDS

119020-03-0Relevant articles and documents

Apoptotic protein inhibitor as well as preparation method and application thereof

-

, (2021/03/23)

The invention relates to a compound with a structure as shown in a formula I which is described in the specification, a racemate, a stereoisomer, a tautomer, an isotope marker, a nitrogen oxide, a solvate, a polymorph, a metabolite, an ester, a prodrug or

Stereoselective synthesis of chiral pyrrolidine derivatives of (+)-α-pinene containing a β-amino acid moiety

Vega-Penaloza, Alberto,Sanchez-Antonio, Omar,Escudero-Casao, Margarita,Tasnadi, Gabor,Fueloep, Ferenc,Juaristi, Eusebio

, p. 2458 - 2468 (2013/09/23)

We report the synthesis of several enantiopure pyrrolidine derivatives containing a β-amino acid moiety. These novel chiral compounds were prepared through stereospecific chlorosulfonyl isocyanate (CSI) addition to the readily available, natural terpene (+)-α-pinene. Coupling of N-Boc-protected β-amino acid derivatives with various bulky amines and amino acids using the mixed anhydride activation method, followed by N-deprotection, afforded the corresponding chiral amino amides in good yields. Despite the severe steric hindrance anticipated in α-pinene-based heterocycles, efficient coupling of the amino amides and an amino ester with the acyl chloride of N-Cbz-protected (S)-proline provided the corresponding pyrrolidinic pinene derivatives in good yields. Moreover, a convenient synthesis of N-Cbz- and N-Boc-monoprotected (S)-prolinamine is reported. Georg Thieme Verlag Stuttgart New York.

Synthesis of chiral NADH analog based on proline template including thiourea and nicotinic acid moieties

Bagdziunas, Gintautas,Haukka, Matti,Butkus, Eugenijus

, p. 2517 - 2523 (2011/08/07)

Chiral reductase-mimicking organic molecule built on proline template incorporating a covalently bound NADH mimic via thiourea, and related reducing agent Hantzsch dihydropyridine, was designed. A synthetic path was developed involving interlinking of chiral proline derivatives with thiourea and subsequent coupling reaction with nicotinoyl chloride. The structure of target compound was studied by x-ray, indicating a double H bond with thiourea hydrogens and oxygen O1 of benzylcarbamate fragment. The reduction of benzil and imines was performed. Taylor & Francis Group, LLC.

Asymmetric organocatalysis of the addition of acetone to 2-nitrostyrene using N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine (PODPEN)

Morris, David J.,Partridge, A. Simon,Manville, Charles V.,Racys, Daugidas T.,Woodward, Gary,Docherty, Gordon,Wills, Martin

supporting information; experimental part, p. 209 - 212 (2010/03/24)

The highly enantioselective addition of acetone to 2-nitrostyrene, using N-diphenylphosphinyl-trans-1,2-diphenylethane-1,2-diamine (PODPEN) as a catalyst, is described.

N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides

Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.

supporting information; experimental part, p. 5260 - 5266 (2009/12/06)

(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.

Enantio- and diastereoselective michael addition reactions of unmodified aldehydes and ketones with nitroolefins catalyzed by a pyrrolidine sulfonamide

Wang, Jian,Li, Hao,Lou, Bihshow,Zu, Liansuo,Guo, Hua,Wang, Wei

, p. 4321 - 4332 (2008/02/06)

Chiral (S)-pyrrolidine trifluoromethanesulfonamide has been shown to serve as an effective catalyst for direct Michael addition reactions of aldehydes and ketones with nitroolefins. A wide range of aldehydes and ketones as Michael donors and nitroolefins as acceptors participate in the process, which proceeds with high levels of enantioselectivity (up to 99% ee) and diastereoselectivity (up to 50:1 d.r.). The methodology has been employed successfully in an efficient synthesis of the potent H., agonist Sen 50917. In addition, a practical three-step procedure for the preparation of (S)-pyrrolidine trifluorometh-anesulfonamide has been developed. The high levels of stereochemical control attending Michael addition reactions catalyzed by this pyrrolidine sulfonamide, have been investigated by using ab initio and density functional methods. Transition state structures for the rate-limiting C-C bond-forming step, corresponding to re- and si-face addition to the reactive conformation of the key enamine intermediates have been calculated. Analysis of these structures indicates that hydrogen bonding plays an important role in catalysis and that the energy barrier for si-face attack in reactions of aldehydes to form 2R,3S products is lower than that for the re-face attack leading to 2S,3R products. In contrast, the energy barrier for re-face addition is lower than that for si-face addition in reactions of ketones. The computational results, which are in good agreement with the experimental observations, are discussed in the context of the stereo-chemical course of these Michael addition reactions.

ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS

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Page/Page column 31-32, (2010/02/15)

The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.

Synthesis of (D)- And (L)-forms of differentially protected 2-piperidinemethanamine

Perumattam, John,Shearer, Barry G.,Confer, William L.,Mathew, Rose M.

, p. 7183 - 7186 (2007/10/02)

(D)- and (L)-isomers of pipecolic acid were converted into (D)- and (L)-2-piperidinemethanamine using an efficient sequence. The amino groups were selectively protected for further functionalization.

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