1-Benzyl-3,4-dihydroxypyrrolidin-1-ium

Base Information

• Chemical Name: 1-Benzyl-3,4-dihydroxypyrrolidin-1-ium
• CAS No.: 90365-74-5
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• Hs Code.: DERIVATION
• DSSTox Substance ID: DTXSID00920431
• Wikidata: Q72442922
• Mol file: 90365-74-5.mol

Synonyms:DTXSID00920431;1-Benzyl-3,4-dihydroxypyrrolidin-1-ium

Chemical Property of 1-Benzyl-3,4-dihydroxypyrrolidin-1-ium

Chemical Property:

• Appearance/Colour: off-white to light brown powder or needles
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Melting Point: 94-100 °C
• Refractive Index: 1.5041 (estimate)
• Boiling Point: 356.2 °C at 760 mmHg
• PKA: 13.99±0.40(Predicted)
• Flash Point: 195.1 °C
• PSA: 43.70000
• Density: 1.27 g/cm³
• LogP: 0.16190
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 194.118103753
• Heavy Atom Count: 14
• Complexity: 170

Purity/Quality:

98% ^*data from raw suppliers

[3S- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(C[NH+]1CC2=CC=CC=C2)O)O
• Isomeric SMILES: C1[C@@H]([C@H](C[NH+]1CC2=CC=CC=C2)O)O
• Uses: (3S,4S)-(+)-1-Benzyl-3,4-pyrrolidinediol can be used:As a building block for the preparation of novel chiral crown ethers.As an intermediate in the synthesis of (3R,4R)1-benzyl-4-fluoropyrrolidin-3- amine.As an intermediate in the preparation of 3-hydroxy-4-pyrrolidinyl analogs of nucleobases.

Technology Process of 1-Benzyl-3,4-dihydroxypyrrolidin-1-ium

There total 16 articles about 1-Benzyl-3,4-dihydroxypyrrolidin-1-ium 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: 98.0%

6-benzyl-2,3-dimethoxy-2,3-dimethylhexahydro-[1,4]dioxino[2,3-c]pyrrole (1031246-25-9) → (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4)

Guidance literature:

With hydrogenchloride; In methanol; at 70 - 80 ℃;

DOI:10.1080/00397910801916520

Reference yield: 93.0%

(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione (75172-31-5) → (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4)

Guidance literature:

With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tet.2006.11.047

Reference yield: 86.59%

(3S,4S)-1-N-benzyl-3,4-dihydroxypyrrolidine-2,6-dione (187032-53-7) → (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 70 ℃; for 3h;

DOI:10.1016/j.bmcl.2017.04.078

upstream raw materials:

benzylamine

rac-1,2,3,4-diepoxybutane

(2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate]

(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione

Downstream raw materials:

(3S,4S)-3,4-Bis<(tert-butyldiphenylsilyl)oxy>-N-benzylpyrrolidine

(3S,4S)-1-benzyl-3,4-bis{[(tert-butyl)dimethylsilyl]oxy}pyrrolidine

(3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine

(3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(trifluoromethanesulfonate)

Refernces

• 1、 Sharma, Ashwani,More, Shahaji H.,Ganesh, Krishna N.. "Electrostatics Favor PNA : DNA Stability over Stereochemistry in Pyrrolidine-Based Cationic Dual-Backbone PNA Analogues". . p. 1146 - 1155. Retrieved 2021/02/09.
• 2、 Katoh, Akira,Kouji, Hiroyuki,Morita, Taiki,Nakamura, Hiroyuki,Umedera, Kohei,Yamada, Kentaro,Yoshimori, Atsushi. "Synthesis of Three-Dimensional (Di)Azatricyclododecene Scaffold and Its Application to Peptidomimetics". supporting information. p. 11888 - 11894. Retrieved 2021/07/06.