dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester

Base Information

• Chemical Name: dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester
• CAS No.: 207276-90-2
• Molecular Formula: C₁₉H₂₉NO₄S₃
• Molecular Weight: 431.642

Synonyms:dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester

Chemical Property of dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester

Chemical Property:

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Technology Process of dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester

There total 7 articles about dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-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: 98.0%

carbon disulfide (75-15-0,12122-00-8) + 6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)-piperidin-3-ol (207276-89-9) + methyl iodide (74-88-4) → dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester (207276-90-2)

Guidance literature:

6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)-piperidin-3-ol; With sodium hydride; In tetrahydrofuran; for 1.5h; Heating;

carbon disulfide; In tetrahydrofuran; for 0.5h; Heating;

methyl iodide; In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1016/S0040-4020(02)01250-4

Reference yield:

(S,E)-4-methyl-N-(2-furylmethylidene)benzenesulfinamide (188447-80-5) → dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester (207276-90-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 83 percent / BF₃*Et₂O / diethyl ether / 2 h / -78 - -40 °C

2.1: 88 percent / mCPBA / CH₂Cl₂ / -30 - 0 °C

3.1: 99 percent / H₂ / Pd/C / ethanol / 6 h

4.1: 74 percent / mCPBA / CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 99 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 20 °C

6.1: NaBH₄ / methanol / -30 °C

6.2: 92 percent / H₂ / Pd/C / ethanol / 27 h

7.1: NaH / tetrahydrofuran / 1.5 h / Heating

7.2: tetrahydrofuran / 0.5 h / Heating

7.3: 98 percent / tetrahydrofuran / 0.5 h / Heating

With sodium tetrahydroborate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium hydride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(02)01250-4

Reference yield:

(S)-N-(1-(furan-2-yl)but-3-en-1-yl)-4-methylbenzenesulfonamide (148409-93-2) → dithiocarbonic acid O-[6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)piperidin-3-yl]ester S-methyl ester (207276-90-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / H₂ / Pd/C / ethanol / 6 h

2.1: 74 percent / mCPBA / CH₂Cl₂ / 3 h / 0 - 20 °C

3.1: 99 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / diethyl ether / 3 h / 0 - 20 °C

4.1: NaBH₄ / methanol / -30 °C

4.2: 92 percent / H₂ / Pd/C / ethanol / 27 h

5.1: NaH / tetrahydrofuran / 1.5 h / Heating

5.2: tetrahydrofuran / 0.5 h / Heating

5.3: 98 percent / tetrahydrofuran / 0.5 h / Heating

With sodium tetrahydroborate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium hydride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(02)01250-4

upstream raw materials:

carbon disulfide

6-ethoxy-2-propyl-1-(toluene-4-sulfonyl)-piperidin-3-ol

methyl iodide

(S)-N-tosyl-α'-propyl-α-furfuryl amine

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