(2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester
• CAS No.: 165672-65-1
• Molecular Formula: C₁₇H₂₅NO₄
• Molecular Weight: 307.39
• Mol file: 165672-65-1.mol

Synonyms:(2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester

Chemical Property of (2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester

There total 14 articles about (2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid 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: 92.0%

(2S,3S,6R)-3-Benzyloxy-6-methoxycarbonylmethyl-2-methyl-piperidine-1-carboxylic acid methyl ester (165672-64-0) → (2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester (165672-65-1)

Guidance literature:

With lithium triethylborohydride;

DOI:10.1016/0040-4039(95)00661-U DOI:10.1021/jo990397t

Reference yield:

benzyl bromide (100-39-0) → (2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester (165672-65-1)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide; benzene / 80 °C

2: 96 percent / Lawesson's reagent / tetrahydrofuran / Heating

3: 83 percent / PPh₃, Et₃N / acetonitrile / Heating

4: 99 percent / NaBH₃CN, TFA / CH₂Cl₂ / 0 °C

5: H₂ / Pd(OH)2 / methanol

6: K₂CO₃ / CH₂Cl₂; H₂O

7: 92 percent / Super-Hydride

With Lawessons reagent; hydrogen; sodium hydride; lithium triethylborohydride; sodium cyanoborohydride; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

Reference yield:

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate (92912-21-5) → (2S,3S,6R)-3-Benzyloxy-6-(2-hydroxy-ethyl)-2-methyl-piperidine-1-carboxylic acid methyl ester (165672-65-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / baker's yeast / H₂O

2: 98 percent / Huenig base / CHCl₃ / Heating

3: 96 percent / Super-Hydride / tetrahydrofuran / 0 °C

4: 95 percent / n-Bu₃P, pyridine

5: 95 percent / Raney Ni (W-4) / ethanol

6: conc. HCl / methanol

7: NaH / dimethylformamide; benzene / 80 °C

8: 96 percent / Lawesson's reagent / tetrahydrofuran / Heating

9: 83 percent / PPh₃, Et₃N / acetonitrile / Heating

10: 99 percent / NaBH₃CN, TFA / CH₂Cl₂ / 0 °C

11: H₂ / Pd(OH)2 / methanol

12: K₂CO₃ / CH₂Cl₂; H₂O

13: 92 percent / Super-Hydride

With Lawessons reagent; pyridine; hydrogenchloride; baker's yeast; tributylphosphine; Raney Ni (W-4); hydrogen; sodium hydride; lithium triethylborohydride; sodium cyanoborohydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

upstream raw materials:

(2S,3S,6R)-3-Benzyloxy-6-methoxycarbonylmethyl-2-methyl-piperidine-1-carboxylic acid methyl ester

benzyl bromide

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate

(5S,6S)-1-Benzyl-5-methoxymethoxy-6-methyl-piperidin-2-one

Downstream raw materials:

(2S,3S,6R)-3-Benzyloxy-6-((Z)-dodeca-2,11-dienyl)-2-methyl-piperidine-1-carboxylic acid methyl ester

(2S,3S,6R)-3-Benzyloxy-2-methyl-6-((Z)-11-oxo-dodec-2-enyl)-piperidine-1-carboxylic acid methyl ester