(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate
• CAS No.: 128510-88-3
• Molecular Formula: C17H25 N O5 S
• Molecular Weight: 355.455
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90471947
• Mol file: 128510-88-3.mol

Synonyms:128510-88-3;(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate;(R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE;tert-butyl (2R)-2-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine-1-carboxylate;tert-Butyl (2R)-2-({[(4-methylbenzene)sulfonyl]oxy}methyl)pyrrolidine-1-carboxylate;(R)-tert-Butyl 2-((tosyloxy)methyl)-pyrrolidine-1-carboxylate;TERT-BUTYL (2R)-2-{[(4-METHYLBENZENESULFONYL)OXY]METHYL}PYRROLIDINE-1-CARBOXYLATE;VSVOPDINJSHSBZ-CQSZACIVSA-N;(R)-Boc-prolinol tosylate;SCHEMBL345625;AMY2489;DTXSID90471947;(R)-tert-Butyl2-((tosyloxy)methyl)pyrrolidine-1-carboxylate;EN300-12578887;(r)-n-t-butoxycarbonyl-2-pyrrolidinylmethyl tosylate;(R)-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine;(R)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester;1,1-dimethylethyl (2R)-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1-pyrrolidinecarboxylate;2-(R)-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester;tert-Butyl (2R)-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1-pyrrolidinecarboxylate;tert-butyl (2R)-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)pyrrolidine-1-carboxylate;tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate;tert-Butyl (R)-2-[[[(4-Methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylate

Chemical Property of (R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Boiling Point: 474.547 °C at 760 mmHg
• PKA: -2.63±0.40(Predicted)
• Flash Point: 240.798 °C
• PSA: 81.29000
• Density: 1.197g/cm³
• LogP: 4.11850
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 355.14534407
• Heavy Atom Count: 24
• Complexity: 526

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl(R)-2-[[[(4-Methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2CCCN2C(=O)OC(C)(C)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2CCCN2C(=O)OC(C)(C)C
• Uses: tert-Butyl (R)-2-[[[(4-Methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylate is an intermediate in the synthesis of (2S)-Ethylpyrrolidine Hydrochloride (E818080), which is used as a reagent in the synthesis of N,N''-substituted-1,3-diamino-2-hydroxypropanes for treating Alzheimer''s disease. Also used as a reagent in the synthesis of cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK kinase inhibitors for treatment of autoimmune disease, cancer, inflammatory disease, and other diseases.

Technology Process of (R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

There total 8 articles about (R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.7%

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) + p-toluenesulfonyl chloride (98-59-9) → tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate (128510-88-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃;

Reference yield: 91.0%

1-(tert-butoxycarbonyl)prolin-2R-ol (59378-81-3,69610-40-8,83435-58-9) + p-toluenesulfonyl chloride (98-59-9) → tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate (128510-88-3)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 8.33333h; Product distribution / selectivity;

Reference yield:

N-(tert-butoxycarbonyl)-D-proline (37784-17-1,59433-50-0) → tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate (128510-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-methylmorpholine / tetrahydrofuran / 0.17 h / -5 °C

2: 0.53 g / I₂; NaBH₄ / tetrahydrofuran / 5.5 h / 0 - 20 °C

3: 78 percent / TEA; DMAP / CH₂Cl₂ / 3 h / 0 °C

With 4-methyl-morpholine; dmap; sodium tetrahydroborate; TEA; iodine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm011059z

upstream raw materials:

1-(tert-butoxycarbonyl)prolin-2R-ol

p-toluenesulfonyl chloride

N-(tert-butoxycarbonyl)-D-proline

N-(tert-butoxycarbonyl)-L-prolinol

Downstream raw materials:

(R)-2-(4-benzylaminophenoxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

(R)-2-[4-(4-iodobenzoyl)phenoxymethyl]pyrrolidine-1-carboxylic acid tert-butyl ester

(R)-2-[4-(4-chlorobenzyl)phenoxymethyl]pyrrolidine-1-carboxylic acid tert-butyl ester

(R)-2-(4-Pyrrol-1-yl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Mahato, Chandan K.,Mukherjee, Sayan,Kundu, Mrinalkanti,Pramanik, Animesh. "Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction". . p. 1053 - 1063. Retrieved 2019/01/14.
• 2、 -. "FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME". Paragraph 00208. . Retrieved 2017/03/08.