(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

Base Information

• Chemical Name: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• CAS No.: 84348-38-9
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• Hs Code.: 2933990090
• Mol file: 84348-38-9.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-methylene-, 1-(1,1-dimethylethyl) ester, (S)-;N-tert-Butoxycarbonyl-4-methylene-L-proline;1-(tert-butoxycarbonyl)-4-methylidene-L-proline;1,2-pyrrolidinedicarboxylic acid, 4-methylene-, 1-(1,1-dimethylethyl) ester, (2S)-;

Chemical Property of (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 110-114 °C
• Refractive Index: 1.513
• Boiling Point: 349.859 °C at 760 mmHg
• PKA: 3.80±0.20(Predicted)
• Flash Point: 165.389 °C
• PSA: 66.84000
• Density: 1.18 g/cm³
• LogP: 1.57450
• Storage Temp.: 2-8°C(protect from light)
• Water Solubility.: Insoluble in water.

Purity/Quality:

98% ^*data from raw suppliers

Boc-4-methylene-L-proline ^*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

Useful:

• Uses: As important intermediates in various areas such as peptide synthesis, asymmetric synthesis, medicinal chemistry, and polymer chemistry. The fluorous prolins were synthesized from commercially available N-Boc-4-methylene- L-proline.

Technology Process of (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

There total 12 articles about (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 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: 85.0%

(S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate (84348-39-0) → (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid (84348-38-9,1427175-11-8)

Guidance literature:

With lithium hydroxide monohydrate; water; In ethanol; at 25 ℃; for 3h;

Reference yield: 78.0%

tert-Butyl (2S)-N-tert-butoxycarbonyl-4-methylideneprolinate (163190-46-3) → (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid (84348-38-9,1427175-11-8)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 32h;

DOI:10.3390/molecules25235644

Reference yield: 65.0%

Methyltriphenylphosphonium bromide (1779-49-3) + N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8) → (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid (84348-38-9,1427175-11-8)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

N-tert-butoxycarbonyl-4-oxo-L-proline; In tetrahydrofuran; at 0 - 20 ℃;

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

methyl triphenylphosphonium bromide

di-tert-butyl dicarbonate

(2S)-4-methylenepyrrolidine-2-carboxylic acid

Downstream raw materials:

N-Boc-4-exomethylene-(S)-prolinyl dibenzyl-(S)-aspartate

tert-Butyl (2S,4R)-tert-butoxycarbonylamino-5-hydroxy-4-tert-butyldiphenylsilyloxymethyl[5,5-2H₂]pentanoate

tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylglutamic acid

Refernces

• 1、 Ariza, Xavier,Bartra, Martí,Berenguer, Ramon,Gómez, Roberto,Garcia, Jordi,López, Blanca,Torralvo, Hèctor. "An enantioselective approach to 4-substituted proline scaffolds: Synthesis of (s)-5-(tert-butoxy carbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid". . . Retrieved 2021/06/14.
• 2、 -. "ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS". Paragraph 0759. . Retrieved 2017/03/14.