114214-69-6

Basic information

• Product Name: 1-Boc-3-hydroxymethylpyrrolidine
• Synonyms: 1-tert-Butoxycarbonylpyrrolidine-3-methanol;1-BOC-3-Hydroxymethyl-1H-pyrrolidine;tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate(SALTDATA: FREE);1-Boc-3-(hydroxyMethyl)py...;N-tert-Butoxycarbonyl-3-(hydroxyMethyl)pyrrolidine;N-Boc-DL-^b-prolinol, 97+%;tert-butyl 3-(hydroxyMethyl)-1-pyrrolidinecarboxylate;N-Boc-DL-beta-prolinol
• CAS NO: 114214-69-6
• Molecular Formula: C₁₀H₁₉NO₃
• Molecular Weight: 201.26
• Product Categories: pharmacetical;Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 114214-69-6.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 285-291℃
• Flash Point: 128.9 °C
• Appearance: /
• Density: 1.089
• Vapor Pressure: 0.000241mmHg at 25°C
• Refractive Index: 1.4680 to 1.4720
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.93±0.10(Predicted)
• CAS DataBase Reference: 1-Boc-3-hydroxymethylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-3-hydroxymethylpyrrolidine(114214-69-6)
• EPA Substance Registry System: 1-Boc-3-hydroxymethylpyrrolidine(114214-69-6)

Safety Data

• Hazard Codes: Xi,N,T
• Statements: 25-50
• Safety Statements: 24/25-61-45
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 114214-69-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Boc-3-hydroxymethylpyrrolidine is used as a key intermediate for the synthesis of SR 9009, a synthetic REV-ERB agonist, for its potential application in the treatment of sleep disorders and metabolic diseases. The compound's role in the development of SR 9009 highlights its importance in regulating circadian behavior and metabolism, making it a valuable component in the pharmaceutical sector.

InChI:InChI=1/C10H19NO3/c1-10(2,3)14-9(13)11-5-4-8(6-11)7-12/h8,12H,4-7H2,1-3H3

Upstream product

• 85310-69-6 pyrrolidin-3-ylmethanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 50-00-0 formaldehyd 
• 1234576-81-8 3-iodo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 59378-87-9 pyrrolidine-3-carboxylic acid 
• 98548-90-4 methyl pyrrolidine-3-carboxylate 
• 35309-35-4 5-oxopyrrolidine-3-carboxylic acid methyl ester 
• 617-52-7 Dimethyl itakonate 
• 103057-44-9 N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine 
• 59379-02-1 tert-butyl 3-formylpyrrolidine-1-carboxylate 
• 201230-82-2 carbon monoxide 
• 73286-71-2 N-(tert-butoxycarbonyl)-2,3-dihydropyrrole 
• 72925-16-7 1-boc-pyrrolidine-3-carboxylic acid 
• 170844-49-2 1-t-butyloxycarbonylpyrrole-3-carboxylic acid ethyl ester 

Downstream Products

• 141699-56-1 3-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 305329-97-9 3-bromomethylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 138108-72-2 tert-butyl (R)-3-hydroxymethylpyrrolidine-1-carboxylate 
• 199174-24-8 tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 276872-88-9 (+/-)-3-[4-(4-flourophenylmethyl)piperidinomethyl]-pyrrolidine 
• 479622-23-6 (2S,3R)-3-(1-{Benzyloxycarbonylamino-[(E)-benzyloxycarbonylimino]-methyl}-pyrrolidin-3-ylmethyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester 
• 479622-22-5 3-((2S,3R)-2-Benzyloxycarbonyl-4-oxo-azetidin-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 420786-27-2 3-(4-methoxycarbonylmethoxy-3-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 59379-02-1 tert-butyl 3-formylpyrrolidine-1-carboxylate 
• 114214-70-9 tert-butyl 3-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine-1-carboxylate 
• 1027594-37-1 3-(benzenesulfonylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

TRPML MODULATORS

The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon

Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.

A process for preparing N - Boc - 3 - pyrrolidine of formaldehyde (by machine translation)

The invention discloses a method for preparing N - Boc - 3 - pyrrolidine of formaldehyde, comprising the following steps: (1) in the solvent is added in chloromethane-based [...] and triphenyl phosphate reaction, to obtain the benzyloxy methyl trityl chloride; (2) the benzyloxy methyl trityl chloride by adding solvent, under alkaline conditions, adding N - Boc - 3 - pyrrolidone reaction, to obtain compound N - Boc - 3 - benzyloxy methylene pyrrolidine; (3) high-pressure container for adding a solvent, N - Boc - 3 - benzyloxy methylene pyrrolidine and catalyst, hydrogenation reaction to obtain N - Boc - 3 - pyrrolidine methanol; (4) will be N - Boc - 3 - pyrrolidine methanol dissolved in dichloromethane solvent, adding Dess - Martin oxidizer to carry out oxidizing, get N - Boc - 3 - pyrrolidine formaldehyde. The method of the invention has the following advantages: the used raw materials low toxicity, easy, low cost, consumption, high yield, few by-products, easy large-scale production. (by machine translation)

Method for synthesizing N-Boc-3-pyrrolidine formaldehyde

The invention discloses a method for synthesizing N-Boc-3-pyrrolidine formaldehyde. The method comprises that dimethyl itaconate as a raw material undergoes an intramolecular cyclization reaction to produce methyl 5-oxo-3-pyrrolidine carboxylate, then the methyl 5-oxo-3-pyrrolidine carboxylate undergoes a reduction reaction to produce pyrrolidine-3-methanol, then the pyrrolidine-3-methanol is subjected to Boc protection so that N-Boc-pyrrolidine-3-methanol is obtained, and finally, the N-Boc-pyrrolidine-3-methanol is oxidized to form a final product compound. The method is simple and convenient, has a low cost, content greater than 99%, produces small environmental pollution and is suitable for industrial production.

Enantioselective Fluorination of Spirocyclic β-Prolinals Using Enamine Catalysis

A series of spirocyclic carbaldehydes were successfully fluorinated using enamine catalysis, furnishing the corresponding tertiary fluorides in both high yields and enantioselectivities. The fluorinated spirocycles provide a set of novel building blocks interesting from a medicinal chemistry point of view.

A structure-guided optimization of pyrido[2,3-d]pyrimidin-7-ones as selective inhibitors of EGFRL858R/T790Mmutant with improved pharmacokinetic properties

Structural optimization of pyrido[2,3-d]pyrimidin-7-ones was conducted to yield a series of new selective EGFRT790Minhibitors with improved pharmacokinetic properties. One of the most promising compound 9s potently suppressed EGFRL858R/T790Mkinase and inhibited the proliferation of H1975?cells with IC50values of 2.0?nM and 40?nM, respectively. The compound dose-dependently induced reduction of the phosphorylation of EGFR and downstream activation of ERK in NCI[sbnd]H1975?cells. It also exhibited moderate plasma exposure after oral administration and an oral bioavailability value of 16%. Compound 9s may serve as a promising lead compound for further drug discovery overcoming the acquired resistance of non-small cell lung cancer (NSCLC) patients.

Preparation method of 1-BOC-3-hydroxymethyl pyrrolidine

The invention discloses a preparation method of 1-Boc-3-hydroxymethyl pyrrolidine. The preparation method uses epichlorohydrin as a raw material, 3-hydroxymethyl pyrrolidine is obtained through reduction and cyclization reaction, then the 1-Boc-3-hydroxymethyl pyrrolidine is prepared through Boc protection reaction, then 1-BOC-3-methyl formate pyrrolidine is prepared through carboxylation reaction and esterification reaction, and finally the 1-BOC-3-methyl formate pyrrolidine and lithium aluminum hydride are catalyzed by a catalyst to prepare the 1-BOC-3-hydroxymethyl pyrrolidine. The preparation method is high in product synthesis rate, high in product purity and low in production cost, and the raw materials are cheap and easy to obtain.

POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS

Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

HETEROCYCLIC COMPOUNDS AS NAV CHANNEL INHIBITORS AND USES THEREOF

The present invention relates to heterocyclic compounds of formula (I) wherein: Z1 is C(R)(R), C(O), C(S), or C(NR); 2 Z is C(R)(R), 0, S, SO, S02, or NR; X is -O-, -S-, -S02-, -SO-, -C(O)-, -C02-, -C(O)N(R)-, -NRC(O)-, -NRC(O) N(R)-, -NRSO2-, or -N(R)-; or X is absent; A is an optionally substituted C1_6 aliphatic, C5-10 aryl, 3-8 membered saturated or partially unsaturated carbocyclic ring, 3-7 membered heterocylic ring, or a 5-6 membered heteroaryl ring; Y is -CH2-, -O-, -S-, -S02-, -SO-, -C(O)-, -C02-, -C(O)N(R)-, -NRC(O)-, - NRC(O)N(R)-, -NRS02-, or -N(R)-; B is an optionally substituted C5-10 aryl or 5-6 membered heteroaryl ring; m is 0, 1, 2, or 3; n is 0, 1, 2, or 3; q is 0, 1, 2, or 3; and r is 1 or 2; and pharmaceutically acceptable compositions thereof, useful as Navl.6 inhibitors.