1-Boc-2-Formylpyrrolidine

Base Information

• Chemical Name: 1-Boc-2-Formylpyrrolidine
• CAS No.: 117625-90-8
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40401032
• Nikkaji Number: J876.208B
• Mol file: 117625-90-8.mol

Synonyms:1-Boc-2-Formylpyrrolidine;117625-90-8;tert-butyl 2-formylpyrrolidine-1-carboxylate;N-tert-Butoxycarbonylpyrrole-2-carboxaldehyde;2-Formyl-pyrrolidine-1-carboxylic acid tert-butyl ester;1-Boc-2-formyl-pyrrolidine;MFCD03790896;59378-82-4;1-Boc-pyrrolidine-2-carbaldehyde;1-Pyrrolidinecarboxylic acid, 2-formyl-, 1,1-dimethylethyl ester;2-Formylpyrrolidine-1-carboxylic acid tert-butyl ester;SCHEMBL190173;DTXSID40401032;YDBPZCVWPFMBDH-UHFFFAOYSA-N;N-(Tert-Butoxycarbonyl)-d-prolnal;AKOS006230071;AB16165;AC-7660;AM90809;CS-W018592;SB31020;SB40798;DS-10417;SY015934;SY022070;SY028283;BB 0263022;FT-0650649;FT-0689465;FT-0689584;tert-butyl?2-formylpyrrolidine-1-carboxylate;EN300-86375;3-AMINO-3-(3-ISOPROPOXYPHENYL)PROPANOICACID;J-504340;J-523183;2-formyl -pyrrolidine-1-carboxylic acid tert-butyl ester;2-formyl-pyrrolidine-l-carboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylicacid, 2-formyl-, 1,1-dimethylethyl ester, (2R)-;InChI=1/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h7-8H,4-6H2,1-3H

Chemical Property of 1-Boc-2-Formylpyrrolidine

Chemical Property:

• Boiling Point: 276.345 °C at 760 mmHg
• PKA: -3.03±0.40(Predicted)
• Flash Point: 120.929 °C
• PSA: 46.61000
• Density: 1.148 g/cm³
• LogP: 1.52270
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 199.12084340
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

1-Boc-2-Formylpyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C=O

Technology Process of 1-Boc-2-Formylpyrrolidine

There total 71 articles about 1-Boc-2-Formylpyrrolidine 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: 100.0%

tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate (115186-37-3) → Boc-L-Pro-H (69610-41-9,117625-90-8)

Guidance literature:

With lithium aluminium tetrahydride; at 0 ℃; for 0.25h;

DOI:10.1081/NCN-100002563

Reference yield: 100.0%

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → Boc-L-Pro-H (69610-41-9,117625-90-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In triethylamine;

DOI:10.1016/S0957-4166(00)82319-8

Reference yield: 99.0%

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → Boc-L-Pro-H (69610-41-9,117625-90-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

upstream raw materials:

N-Boc-prolinol

(S)-N-(tert-butoxycarbonyl)proline methyl ester

tert-butyl pyrrolidine-1-carboxylate

N,N-dimethyl-formamide

Downstream raw materials:

2-(R)-Vinyl-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

(S) 2-(1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-prolinol

(R)-2-ethynyl-1-pyrrolidinecarboxylic acid,1,1-dimethylethyl ester

Refernces

• 1、 Tang, Yongquan,Dong, Ke,Wang, Sai,Sun, Qi,Meng, Xiangju,Xiao, Feng-Shou. "Boosting the hydrolytic stability of phosphite ligand in hydroformylation by the construction of superhydrophobic porous framework". . . Retrieved 2019.
• 2、 Garvey, David S.,Wasicak, James T.,Chung, John Y.-L.,Shue, Youe-Kong,Carrera, George M.,et al.. "Synthesis and in Vitro Characterization of Novel Amino Terminally Modified Oxotremorine Derivatives for Brain Muscarinic Receptors". . p. 1550 - 1557. Retrieved 1992.
• 3、 Beckett, R. Paul,Davies, Stephen G.,Mortlock, Andrew A.. "Asymmetric synthesis of (1R,8S)- and (1S,8S)-1-Hydroxypyrrolizidin-3-ones via the aldol reaction between N-Boc-(S)-Prolinal and chiral acetate enolate equivalents derived from (S)- and (R)-5-C5H5)Fe(CO)(PPh3)COCH3>". . p. 123 - 136. Retrieved 1992.
• 4、 Grudzień, Krzysztof,Noga?, Wojciech,Szczepaniak, Grzegorz,Grela, Karol. "Larger scale Stahl oxidation with instant Cu removal in convenient synthesis of chiral bidentate N–heterocyclic carbene precursor". . . Retrieved 2021.
• 5、 Sibi, Mukund P.,Christensen, James W.. "Enantiospecific Synthesis of (-)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine 1". . p. 6434 - 6442. Retrieved 1999.
• 6、 Sibi, Mukund P.,Christensen, James W.,Li, Biqin,Renhowe, Paul A.. "A Novel Thermolytic Annulation of an Oxazolidinone: An Enantiospecific Synthesis of (-)-Slaframine". . p. 4329 - 4330. Retrieved 1992.
• 7、 Vasta, James D.,Choudhary, Amit,Jensen, Katrina H.,McGrath, Nicholas A.,Raines, Ronald T.. "Prolyl 4-hydroxylase: Substrate isosteres in which an (E)- or (Z)-alkene replaces the prolyl peptide bond". . p. 219 - 227. Retrieved 2017.
• 8、 Siegrist, Romain,Baumgartner, Corinne,Seiler, Paul,Diederich, Francois. "Facile synthesis of diastereoisomerically and optically pure 2-substituted hexahydro-1H-pyrrolizin-3-ones". . p. 2250 - 2261. Retrieved 2005.
• 9、 Kolodyazhnaya,Kolodyazhnaya,Kolodyazhnyi. "Synthesis of phosphonic analog of (S)-homoproline". . p. 169 - 170. Retrieved 2014.
• 10、 Ibuka, Toshiro,Taga, Tooru,Habashita, Hiromu,Nakai, Kazuo,Tamamura, Hirokazu,et al.. "Syn-SN2' Pathway in the Reaction of Certain γ-(Mesyloxy)α,β-Enoates with RCu(CN)MgX*BF3 Reagents. Importance of MgX and Bulky R Group upon the Diastereoselectivity". . p. 1207 - 1214. Retrieved 1993.