(R)-tert-butyl 3-formylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: (R)-tert-butyl 3-formylpyrrolidine-1-carboxylate
• CAS No.: 59379-02-1
• Molecular Formula: C10H17NO3
• Molecular Weight: 199.25
• Hs Code.: 2933990090
• European Community (EC) Number: 635-408-3
• DSSTox Substance ID: DTXSID00974792
• Nikkaji Number: J3.412.461B
• Wikidata: Q72450641
• Mol file: 59379-02-1.mol

Synonyms:191347-94-1;(R)-tert-butyl 3-formylpyrrolidine-1-carboxylate;(R)-1-Boc-3-pyrrolidinecarbaldehyde;tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate;(3R)-3-FORMYL-1-PYRROLIDINECARBOXYLIC ACID TERT-BUTYL ESTER;1-Pyrrolidinecarboxylic acid, 3-formyl-, 1,1-dimethylethyl ester, (R)-;(R)-1-Boc-pyrrolidine-3-carbaldehyde;MFCD14635728;SCHEMBL935410;DTXSID00974792;(3R)-1-Boc-3-formylpyrrolidine;(R)-3-formyl-1-Boc-pyrrolidine;(r)-1-boc-3-pyrrolidinecarboxaldehyde;AKOS024262357;AM86014;AS-42180;CS-0048573;A26498;(R)-tert-butyl3-formylpyrrolidine-1-carboxylate;EN300-1697197;(R)-3-Formylpyrrolidine-1-carboxylic Acid t-Butyl Ester;(3R)-3alpha-Formyltetrahydro-1H-pyrrole-1-carboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylic acid, 3-formyl-, 1,1-dimethylethyl ester, (3R)-

Chemical Property of (R)-tert-butyl 3-formylpyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.00483mmHg at 25°C
• Refractive Index: 1.528
• Boiling Point: 276.3 °C at 760 mmHg
• PKA: -2.44±0.40(Predicted)
• Flash Point: 120.9 °C
• PSA: 46.61000
• Density: 1.148 g/cm³
• LogP: 1.38020
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• 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:

98% ^*data from raw suppliers

1-Boc-3-formyl-pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-51-36-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C1)C=O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@H](C1)C=O
• Uses: 1-Boc-pyrrolidine-3-carboxaldehyde is used in the preparation of tertiary amines as agonists of the nuclear hormone receptor Rev-erbα.

Technology Process of (R)-tert-butyl 3-formylpyrrolidine-1-carboxylate

There total 13 articles about (R)-tert-butyl 3-formylpyrrolidine-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: 93.0%

tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (114214-69-6) → tert-butyl 3-formylpyrrolidine-1-carboxylate (59379-02-1,191348-04-6)

Guidance literature:

With manganese(IV) oxide; In dimethyl sulfoxide; at 20 ℃; for 24h; Solvent; Reagent/catalyst;

Reference yield:

tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (569667-93-2) → tert-butyl 3-formylpyrrolidine-1-carboxylate (59379-02-1,191348-04-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

Reference yield:

carbon monoxide (201230-82-2) + N-(tert-butoxycarbonyl)-2,3-dihydropyrrole (73286-71-2) → N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde (59378-82-4,117625-90-8) + tert-butyl 3-formylpyrrolidine-1-carboxylate (59379-02-1,191348-04-6)

Guidance literature:

With tris(2,4-di-tert-butylphenyl)phosphite; hydrogen; acetylacetonatodicarbonylrhodium(l); In toluene; at 50 ℃; for 4h; under 7500.75 Torr; Further Variations:; Reagents; Product distribution;

DOI:10.1039/b315709a

upstream raw materials:

tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

carbon monoxide

N-(tert-butoxycarbonyl)-2,3-dihydropyrrole

N-(tert-butoxycarbonyl)-3-pyrroline

Downstream raw materials:

3-(benzenesulfonyl-tert-butoxycarbonylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]pyrrolidine-1-carboxylate

Refernces

• 1、 Ning, Xiang-Li,Li, Yu-Zhi,Huo, Cui,Deng, Ji,Gao, Cheng,Zhu, Kai-Rong,Wang, Miao,Wu, Yu-Xiang,Yu, Jun-Lin,Ren, Ya-Li,Luo, Zong-Yuan,Li, Gen,Chen, Yang,Wang, Si-Yao,Peng, Cheng,Yang, Ling-Ling,Wang, Zhou-Yu,Wu, Yong,Qian, Shan,Li, Guo-Bo. "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". supporting information. p. 8303 - 8332. Retrieved 2021/06/30.
• 2、 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 2019/06/05.