N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester
• CAS No.: 184046-78-4
• Molecular Formula: C11H19NO5
• Molecular Weight: 245.276
• Mol file: 184046-78-4.mol

Synonyms:(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxyproline methyl ester;N-tert-butoxycarbonyl-(2S,3S)-3-hydroxyproline methyl ester;(2S,3S)-N-tert-butoxycarbonyl-3-hydroxy-2-pyrrolidine carboxylic acid methyl ester;N-(TERT-BUTOXYCARBONYL)-(3S)-HYDROXY-L-PROLINE METHYL ESTER;N-tert-butoxycarbonyl-trans-3-hydroxy-L-proline methyl ester;VT1198;(2S,3S)-1-tert-butyl 2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate;methyl 1-(tert-butoxycarbonyl)-(3S)-hydroxypyrrolidine-2-carboxylate;(2S,3S)-1-(TERT-BUTOXYCARBONYL)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER;BOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER;(2S,3S)-N-tert-butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic acid methyl ester;

Chemical Property of N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester

Chemical Property:

• Vapor Pressure: 8.47E-06mmHg at 25°C
• Boiling Point: 335.2oC at 760 mmHg
• PKA: 14.03±0.40(Predicted)
• Flash Point: 156.6oC
• PSA: 76.07000
• Density: 1.216
• LogP: 0.46760
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(2S,3S)-3-Hydroxy-1,2-pyrrolidinedicarboxylicacid1-tert-Butyl2-MethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,3S)-3-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester is a reactant used to improve potency of imidazo[1,2-b]pyridazines as IKKβ inhibitors.

Technology Process of N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl ester

There total 19 articles about N-(tert-Butoxycarbonyl)-(3S)-hydroxy-L-proline methyl 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: 100.0%

(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (187039-57-2,335280-19-8) + diazomethyl-trimethyl-silane (18107-18-1) → (2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate (184046-78-4)

Guidance literature:

In tetrahydrofuran; methanol; diethyl ether; at 0 ℃; for 2h; Product distribution / selectivity;

Reference yield: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (187039-57-2,335280-19-8) → (2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate (184046-78-4)

Guidance literature:

In methanol; diethyl ether; at 20 ℃; for 0.25h;

DOI:10.1021/ol0161054

Reference yield: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (1844898-16-3) → (2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate (184046-78-4)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20 ℃; Inert atmosphere; Cooling with ice bath;

upstream raw materials:

di-tert-butyl dicarbonate

methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate

diazomethane

(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Downstream raw materials:

N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester

methyl (3S)-benzyloxy-1-(tert-butoxycarbonyl)pyrrolidine-(2S)-carboxylate

C₆H₁₁NO₃*CF₃COOH

(2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine