(S)-Ethyl 4-benzyl-5-oxomorpholine-3-carboxylate

Base Information

• Chemical Name: (S)-Ethyl 4-benzyl-5-oxomorpholine-3-carboxylate
• CAS No.: 106973-40-4
• Molecular Formula: C14H17 N O4
• Molecular Weight: 263.29
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60543342
• Wikidata: Q82420183
• Mol file: 106973-40-4.mol

Synonyms:106973-40-4;(S)-Ethyl 4-benzyl-5-oxomorpholine-3-carboxylate;(S)-ETHYL 4-BENZYL-5-OXO-MORPHOLINE-3-CARBOXYLATE;Ethyl (3S)-4-benzyl-5-oxomorpholine-3-carboxylate;ethyl (S)-4-benzyl-5-oxomorpholine-3-carboxylate;(S)-4-Benzyl-5-oxo-morpholine-3-carboxylic acid ethyl ester;(S)-Ethyl4-benzyl-5-oxomorpholine-3-carboxylate;DTXSID60543342;MFCD09878824;CS-0339526

Chemical Property of (S)-Ethyl 4-benzyl-5-oxomorpholine-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.07E-07mmHg at 25°C
• Melting Point: 77-78 °C(Solv: ligroine (8032-32-4))
• Refractive Index: 1.542
• Boiling Point: 432.9°Cat760mmHg
• PKA: -2.83±0.40(Predicted)
• Flash Point: 215.6°C
• PSA: 55.84000
• Density: 1.21g/cm³
• LogP: 0.91500
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

97% ^*data from raw suppliers

(S)-Ethyl4-benzyl-5-oxomorpholine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1COCC(=O)N1CC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@@H]1COCC(=O)N1CC2=CC=CC=C2

Technology Process of (S)-Ethyl 4-benzyl-5-oxomorpholine-3-carboxylate

There total 3 articles about (S)-Ethyl 4-benzyl-5-oxomorpholine-3-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: 94.0%

ethanol (64-17-5) + (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (106973-37-9) → ethyl (S)-5-oxo-4-(phenylmethyl)morpholine-3-carboxylate (106973-40-4)

Guidance literature:

With thionyl chloride; at 20 ℃; for 1h;

DOI:10.1002/hlca.200490021

Reference yield:

benzaldehyde (100-52-7) → ethyl (S)-5-oxo-4-(phenylmethyl)morpholine-3-carboxylate (106973-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) sodium hydroxide (2 M); 2) sodium borohydride / 1) 30 min; 2) 6-10 deg C, 1+1+1+2 h

2: 28 percent / sodium hydroxide / H₂O / 0 deg C, 30 min, 30-33 deg C, 2 h

3: 16 percent / pyridine, phenyl dichlorophosphate / 1,2-dimethoxy-ethane / 18 h

With pyridine; sodium hydroxide; sodium tetrahydroborate; O-phenyl phosphorodichloridate; In 1,2-dimethoxyethane; water;

Reference yield:

(S)-2-(benzylamino)-3-hydroxypropanoic acid (106910-76-3,106910-77-4,17136-45-7) → ethyl (S)-5-oxo-4-(phenylmethyl)morpholine-3-carboxylate (106973-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOH / 0.5 h

1.2: 40 percent / NaOH / 2 h

2.1: 94 percent / SOCl₂ / 1 h / 20 °C

With sodium hydroxide; thionyl chloride;

DOI:10.1002/hlca.200490021

upstream raw materials:

ethanol

(3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

(S)-2-(benzylamino)-3-hydroxypropanoic acid

benzaldehyde

Downstream raw materials:

(S)-3-(bromomethyl)-4-(phenylmethyl)morpholine

(S)-3-{[(phenylmethyl)sulfanyl]methyl}morpholine

(S)-4-(phenylmethyl)-3-{[(phenylmethyl)sulfanyl]methyl}morpholine

2,2,2-trichloro (S)-3-{[(phenylmethyl)sulfanyl]methyl}morpholine-4-carboxylate

Refernces

• 1、 Brown, George R.,Foubister, Alan J.,Wright, Brian. "Chiral Synthesis of 3-Substituted Morpholines via Serine Enantiomers and Reductions of 5-Oxomorpholine-3-carboxylates". . p. 2577 - 2580. Retrieved 2007/10/02.