(2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 259133-72-7
• Molecular Formula: C₂₁H₃₁NO₄S
• Molecular Weight: 393.547
• Mol file: 259133-72-7.mol

Synonyms:(2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester

There total 16 articles about (2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl 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: 88.0%

phenylcarbonochloridothioate (1005-56-7) + (2R,6R)-2-hydroxymethyl-6-propyl-N-Boc-piperidine (259133-71-6) → (2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester (259133-72-7)

Guidance literature:

With dmap; In dichloromethane; for 5.5h;

DOI:10.1021/ol9912534

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester (259133-72-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 79 percent / DMAP / acetonitrile

2.1: 94 percent / DIBALH / CH₂Cl₂; hexane / 3 h / -78 °C

3.1: 86 percent / p-TsOH / toluene / 0.33 h

4.1: n-BuLi; TMEDA / tetrahydrofuran; hexane / -65 - -30 °C

4.2: 52 percent / tetrahydrofuran; hexane / 0.08 h / -78 °C

5.1: 87 percent / H₂ / (S)-BINAP; RuCl₂ / methanol / 11 h / 45 °C / 51716.2 Torr

6.1: 97 percent / BH₃*THF / tetrahydrofuran / 3 h / 20 °C

7.1: 98 percent / oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - 20 °C

8.1: 79 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

9.1: 98 percent / H₂ / Pd/C / ethyl acetate / 24 h

10.1: s-BuLi; TMEDA

11.1: silica gel

12.1: 85 percent / NaBH₄ / ethanol / 20 - 70 °C

13.1: 88 percent / DMAP / CH₂Cl₂ / 5.5 h

With dmap; sodium tetrahydroborate; n-butyllithium; borane-THF; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; sec.-butyllithium; silica gel; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; ruthenium(II) chloride; dmap; palladium on activated charcoal; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; 1.1: Substitution / 2.1: Reduction / 3.1: Dehydration / 4.1: Metallation / 4.2: Carboxylation / 5.1: Reduction / 6.1: Reduction / 7.1: Oxidation / 8.1: Wittig reaction / 9.1: Catalytic hydrogenation / 10.1: Formylation / 11.1: Isomerization / 12.1: Reduction / 13.1: Condensation;

DOI:10.1021/ol9912534

Reference yield:

N-tert-butoxycarbonyl-3-piperidinol (85275-45-2) → (2R,6R)-2-Phenoxythiocarbonyloxymethyl-6-propyl-piperidine-1-carboxylic acid tert-butyl ester (259133-72-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 89 percent / NaH / tetrahydrofuran / 6 h / 20 °C

2.1: s-BuLi; TMEDA / tetrahydrofuran; cyclohexane / 5 h / -78 °C

2.2: 80 percent / tetrahydrofuran; cyclohexane / 0.08 h / -78 °C

3.1: 87 percent / H₂ / (S)-BINAP; RuCl₂ / methanol / 11 h / 45 °C / 51716.2 Torr

4.1: 97 percent / BH₃*THF / tetrahydrofuran / 3 h / 20 °C

5.1: 98 percent / oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - 20 °C

6.1: 79 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

7.1: 98 percent / H₂ / Pd/C / ethyl acetate / 24 h

8.1: s-BuLi; TMEDA

9.1: silica gel

10.1: 85 percent / NaBH₄ / ethanol / 20 - 70 °C

11.1: 88 percent / DMAP / CH₂Cl₂ / 5.5 h

With dmap; sodium tetrahydroborate; n-butyllithium; borane-THF; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; sec.-butyllithium; silica gel; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; ruthenium(II) chloride; palladium on activated charcoal; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; ethyl acetate; 1.1: Methylation / 2.1: Dehydration / 2.2: Carboxylation / 3.1: Reduction / 4.1: Reduction / 5.1: Oxidation / 6.1: Wittig reaction / 7.1: Catalytic hydrogenation / 8.1: Formylation / 9.1: Isomerization / 10.1: Reduction / 11.1: Condensation;

DOI:10.1021/ol9912534

upstream raw materials:

phenylcarbonochloridothioate

(2R,6R)-2-hydroxymethyl-6-propyl-N-Boc-piperidine

piperidin-2-one

di-tert-butyl dicarbonate