(S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone

Base Information

• Chemical Name: (S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone
• CAS No.: 175609-12-8
• Molecular Formula: C₁₃H₁₃NO₂S
• Molecular Weight: 247.318
• Mol file: 175609-12-8.mol

Synonyms:(S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone

Chemical Property of (S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone

There total 7 articles about (S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone 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: 70.0%

Benzoic acid (S)-6-oxo-1,2,3,6-tetrahydro-pyridin-2-ylmethyl ester (175609-11-7) → (S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone (175609-12-8)

Guidance literature:

With Lawessons reagent; In toluene; at 60 ℃; for 0.166667h;

DOI:10.7164/antibiotics.49.155

Reference yield:

benzoyl chloride (98-88-4) → (S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone (175609-12-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 47 percent / pyridine; CH₂Cl₂ / 5 h / -40 - 0 °C

2: 1) NaH / 1) THF, room temperature, 1 h, 2) 1.5 h

3: 1) lithium bis(trimethylsilyl) amide / 1) THF, -78 deg C, 20 min, 2) -78 deg C, 40 min, -78 deg C -> room temperature, 1h

4: NaHCO₃, 30percent H₂O₂ / ethyl acetate; tetrahydrofuran / 1 h

5: 1.9 g / trifluoroacetic acid / H₂O / 1 h

6: 70 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphethane-2,4-disulfide / toluene / 0.17 h / 60 °C

With Lawessons reagent; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate; toluene;

DOI:10.7164/antibiotics.49.155

Reference yield:

(+)-(S)-6-hydroxymethyl-2-piperidinone (128726-47-6) → (S)-(-)-3,4-dehydro-6-benzoyloxymethyl-2-thiopiperidinone (175609-12-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 47 percent / pyridine; CH₂Cl₂ / 5 h / -40 - 0 °C

2: 1) NaH / 1) THF, room temperature, 1 h, 2) 1.5 h

3: 1) lithium bis(trimethylsilyl) amide / 1) THF, -78 deg C, 20 min, 2) -78 deg C, 40 min, -78 deg C -> room temperature, 1h

4: NaHCO₃, 30percent H₂O₂ / ethyl acetate; tetrahydrofuran / 1 h

5: 1.9 g / trifluoroacetic acid / H₂O / 1 h

6: 70 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphethane-2,4-disulfide / toluene / 0.17 h / 60 °C

With Lawessons reagent; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate; toluene;

DOI:10.7164/antibiotics.49.155

upstream raw materials:

Benzoic acid (S)-6-oxo-1,2,3,6-tetrahydro-pyridin-2-ylmethyl ester

benzoyl chloride

(+)-(S)-6-hydroxymethyl-2-piperidinone

Benzoic acid (S)-6-oxo-piperidin-2-ylmethyl ester

Downstream raw materials:

(S)-(-)-3,4-dehydro-6-hydroxymethyl-2-thiopiperidinone

Refernces