L-Proline, 5-ethenyl-, methyl ester, (5R)-

Base Information

• Chemical Name: L-Proline, 5-ethenyl-, methyl ester, (5R)-
• CAS No.: 210345-07-6
• Molecular Formula: C8H13 N O2
• Molecular Weight: 155.19432
• DSSTox Substance ID: DTXSID70473989
• Nikkaji Number: J1.412.637F
• Wikidata: Q82303720
• Mol file: 210345-07-6.mol

Synonyms:210345-07-6;L-PROLINE, 5-ETHENYL-, METHYL ESTER, (5R)-;SCHEMBL18467878;DTXSID70473989;AKOS015954717;L-Proline,5-ethenyl-,methyl ester,(5R)-(9ci)

Chemical Property of L-Proline, 5-ethenyl-, methyl ester, (5R)-

Chemical Property:

• Boiling Point: 198.5±40.0 °C(Predicted)
• PKA: 7.86±0.10(Predicted)
• PSA: 38.33000
• Density: 1.083±0.06 g/cm3(Predicted)
• LogP: 0.79480
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(N1)C=C
• Isomeric SMILES: COC(=O)[C@@H]1CC[C@@H](N1)C=C

Technology Process of L-Proline, 5-ethenyl-, methyl ester, (5R)-

There total 6 articles about L-Proline, 5-ethenyl-, methyl ester, (5R)- 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: 65.0%

(2S,5R)-N-tert-butoxycarbonyl-5-vinylpyrrolidine-2-carboxylic acid methyl ester (328974-66-9) → 5R-vinyl proline methyl ester (210345-07-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4039(98)00858-2

Reference yield:

cis-N-(methoxycarbonyl)-5-<2-(trimethylsilyl)ethynyl>-L-proline methyl ester (138958-09-5) → 5R-vinyl proline methyl ester (210345-07-6)

Guidance literature:

cis-N-(methoxycarbonyl)-5-<2-(trimethylsilyl)ethynyl>-L-proline methyl ester; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -20 ℃;

With hydrogen; Lindlar's catalyst; In ethyl acetate;

With trimethylsilyl iodide; In chloroform; at 50 ℃;

DOI:10.1016/S0040-4020(00)00856-5

Reference yield:

1-carbomethoxy-5-methoxy-L-proline methyl ester (185385-13-1) → 5R-vinyl proline methyl ester (210345-07-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 44 percent / SnCl₄; AlCl₃ / CH₂Cl₂ / 36 h / 20 °C

2.1: TBAF / tetrahydrofuran / -20 °C

2.2: H₂ / Lindlar catalyst / ethyl acetate

2.3: TMSI / CHCl₃ / 50 °C

With aluminium trichloride; tetrabutyl ammonium fluoride; tin(IV) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(00)00856-5

upstream raw materials:

(2S,5R)-N-tert-butoxycarbonyl-5-vinylpyrrolidine-2-carboxylic acid methyl ester

cis-N-(methoxycarbonyl)-5-<2-(trimethylsilyl)ethynyl>-L-proline methyl ester

1-carbomethoxy-5-methoxy-L-proline methyl ester

(2S)-5-allyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Downstream raw materials:

(3S,9aR)-6-Benzyloxy-5-oxo-7-phenyl-2,3,5,6,7,9a-hexahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid methyl ester

(3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

(3R,4R,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

(3S,4S,7R,10S)-1-aza-3-t-butoxycarbonylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane