(2S,4R)-1-(tert-butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4R)-1-(tert-butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid
• CAS No.: 273221-97-9
• Molecular Formula: C11H19NO5
• Molecular Weight: 245.27
• DSSTox Substance ID: DTXSID00692964
• Wikidata: Q72510223
• Mol file: 273221-97-9.mol

Synonyms:273221-97-9;(2S,4R)-1-(tert-butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid;BOC-L-TRANSPRO(4-CH2OH);(2S,4R)-1-Boc-4-(hydroxymethyl)-pyrrolidine-2-carboxylic acid;(2S,4R)-4-(hydroxymethyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2S,4R)-1-(Tert-butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylicacid;SCHEMBL7807219;DTXSID00692964;(2S,4R)-1-Boc-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid;YKA22197;MFCD01860673;AS-50434;CS-0053423;P10207;(4R)-1-(tert-Butoxycarbonyl)-4-(hydroxymethyl)-L-proline;(2S,4R)-1-Boc-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid ee;(2S,4R)-1-(t-Butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid

Chemical Property of (2S,4R)-1-(tert-butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 4.24E-08mmHg at 25°C
• Boiling Point: 401°C at 760 mmHg
• Flash Point: 196.3°C
• PSA: 87.07000
• Density: 1.240±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 0.62680
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 245.12632271
• Heavy Atom Count: 17
• Complexity: 310

Purity/Quality:

97% ^*data from raw suppliers

(2S,4R)-1-Boc-4-(hydroxymethyl)pyrrolidine-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)O)CO

Technology Process of (2S,4R)-1-(tert-butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid

There total 2 articles about (2S,4R)-1-(tert-butoxycarbonyl)-4-(hydroxymethyl)pyrrolidine-2-carboxylic acid 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: 88.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxymethylpyrrolidine-1,2-dicarboxylate (220047-92-7) → 4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (273221-97-9)

Guidance literature:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxymethylpyrrolidine-1,2-dicarboxylate; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃;

With hydrogenchloride; In tetrahydrofuran; water; pH=3 - 5;

Reference yield:

1,4-p-tolylsulfanylcarbonyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (630424-90-7) → 4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (273221-97-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 20 °C

2: lithium hydroxide; water / tetrahydrofuran; methanol / 20 °C

With lithium hydroxide; sodium tetrahydroborate; water; In tetrahydrofuran; methanol; ethanol;

upstream raw materials:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxymethylpyrrolidine-1,2-dicarboxylate

1,4-p-tolylsulfanylcarbonyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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