137496-71-0

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-Boc-2-methylpyrrolidine is used as a synthetic building block for the creation of asymmetric organic molecules, which are critical in the development of new pharmaceutical compounds. Its chiral nature allows for the synthesis of enantiomerically pure products, which is essential for ensuring the desired biological activity and minimizing potential side effects in drug candidates.
Used in Organic Chemistry Research:
(S)-1-Boc-2-methylpyrrolidine is used as a versatile reagent in organic chemistry research, enabling the synthesis of a wide range of complex molecules. Its stability and reactivity make it a valuable tool for exploring new reaction pathways and developing innovative synthetic strategies.
Used in Chemical Synthesis:
(S)-1-Boc-2-methylpyrrolidine is used as a key intermediate in the synthesis of various chemical compounds, including those with potential applications in materials science, agrochemicals, and other specialty chemical industries. Its unique structural features facilitate the construction of complex molecular architectures, contributing to the development of novel products and technologies.

InChI:InChI=1/C10H19NO2/c1-8-6-5-7-11(8)9(12)13-10(2,3)4/h8H,5-7H2,1-4H3/t8-/m0/s1

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 77-78-1 dimethyl sulfate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 74-88-4 methyl iodide 
• 128510-88-3 tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate 
• 132482-10-1 (R)-1-<(1,1-dimethylethoxy)carbonyl>-2-pyrrolidinemethanolmethanesulfonate 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 765-38-8 (S)-2-methylpyrrolidine 

Downstream Products

• 765-38-8 (S)-2-methylpyrrolidine 
• 1212353-38-2 (S)-2-methylpyrrolidine 4-methylbenzenesulfonic acid 
• 92012-42-5 (2S,5R)-2,5-Dimethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 156038-84-5 (2S,5S)-2,5-Dimethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

The Configuration Stability of Chiral Lithio α-Amino Carbanions. The Effect of Li-O vs. Li-N Complexation.

α-Lithio pyrrolidine, as its N-t-BOC or formamidine derivative, has been generated in high enantiomeric purity via Sn-Li exchange of the enantiomerically enriched (88-95percent) α-tributylstannane derivative, 4.The alkylation of these lithio carbanions gave 2-methyl pyrrolidines as well as providing a measure of their configurational stability.It was found that the α-lithio formamidines were configurationally more stable than the t-BOC derivatives and this is attributed to, the stronger O-Li bond which weakens the adjacent C-Li bond, thus allowing configurational decay to occur more readily.This is the first report wherein a difference is observed between O-Li-C and N-Li-C configurational stability.

Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate

We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.

Asymmetric lithiation trapping of N -boc heterocycles at temperatures above -78°C

The asymmetric lithiation trapping of N-Boc heterocycles using s-BuLi/chiral diamines at temperatures up to -20°C is reported. Depending on the N-Boc heterocycle, lithiation is accomplished using s-BuLi and (-)-sparteine or the (+)-sparteine surrogate in the temperature range -50 to -20°C for short reaction times (2-20 min). Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered functionalized N-Boc heterocycles in 47-95% yield and 77:23-93:7 er. With N-Boc pyrrolidine, trapped products can be generated in ～90:10 er even at -20°C.

Asymmetric synthesis of chiral cyclic amine from cyclic imine by bacterial whole-cell catalyst of enantioselective imine reductase

Streptomyces sp. GF3587 and 3546 were found to be imine-reducing strains with high R- and S-selectivity by screening using 2-methyl-1-pyrroline (2-MPN). Their whole-cell catalysts produced 91 mM R-2-methylpyrrolidine (R-2-MP) with 99.2%e.e. and 27.5 mM S-2-MP (92.3%e.e.) from 2-MPN at 91-92% conversion in the presence of glucose, respectively.

LXR AND FXR MODULATORS

Compounds of the invention are disclosed, such as compounds of formulae LX - LXIV, and pharmaceutically acceptable salts, isomers, or prodrugs thereof, which are useful as modulators of the activity of liver X receptors (LXR) and Farnesoid X receptors (FXR), where R00, R200, R400, R500, J11, J21, G1, G21, and Q are defined herein. Pharmaceutical compositions containing the compounds and methods of using the compounds are also disclosed.

OXAZOLE DERIVATIVES AS HISTAMINE H3 RECEPTOR AGENTS, PREPARATION AND THERAPEUTIC USES

The present invention discloses novel aryl oxazole compounds of Formula I (I), or pharmaceutically acceptable salts thereof, which have histamine-H3 receptor antagonist or inverse agonist activity, as well as methods for preparing and using such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula I as well as methods of using these compositions to treat obesity, cognitive deficiencies, narcolepsy, and other histamine H3 receptor-related diseases. Formula I (I) or a pharmaceutically acceptable salt thereof, wherein: m is independenlly at each occurrence 1, 2, or 3, Z independently represents carbon (substituted with hydrogen or the optional substituents indicated herein) or nitrogen, provided that when Z is nitrogen then R6 is not attached to Z; R1 and R2 are independently -(C1-C7) alkyl(optionally substituted with one to three halogens), or R1 and R2 and the nitrogen to which they are attached form an azetidinyl ring, a pyrrolidinyl ring, or a piperidinyl ring, wherein further the azetidinyl, pyrrolidinyl, or piperidinyl ring so formed may be optionally substituted one to three times with R5; R6 is independently at each occurrence -H, -halogen, or -CH3.

Process for preparing 2-methylpyrrolidine and specific enantiomers thereof

The invention relates to a process for preparing 2-methylpyrrolidine and, more particularly, specific enantiomers of 2-methylpyrrolidine. Novel intermediates also are described.

Process for preparing 2-methylpyrrolidine and specific enantiomers thereof

The invention relates to a process for preparing 2-methylpyrrolidine and, more particularly, specific enantiomers of 2-methylpyrrolidine. Novel intermediates also are described.

Complex-induced proximity effects: The effect of varying directing-group orientation on carbamate-directed lithiation reactions

A series of selected bicyclic carbamates in which the range of accessible angles and distances between the carbonyl group and the proton removed in an α-lithiation reaction are structurally defined have been investigated. Oxazolidinones 7-10 undergo stereoselective lithiation-substitution reactions to provide cis-18-27 and cis-31-35 as the major diastereomers. Two series of competition experiments show that the conformationally restricted carbamates 7, 10, 11, and 15 undergo lithiation via complexes more efficiently than Boc amines 4-6. These results along with semiempirical calculations suggest that a small dihedral angle and a calculated distance of 2.78 A between the carbamate carbonyl oxygen and the proton to be removed are favorable for a carbamate-directed lithiation. A series of tin-lithium exchange experiments on cis- and trans-18 and (S)-39 indicate that the configurational stability of a carbamate-stabilized organolithium species may be enhanced by restrictive geometry.

Conversion of chiral amino acids to enantiomerically pure α-methylamines

Enantiomerically enriched α-methylamines are obtained in high yield by Raney nickel reduction of N-Boc-protected, amino acid-derived thioethers.