tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate

Base Information

• Chemical Name: tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate
• CAS No.: 708253-91-2
• Molecular Formula: C₂₃H₄₀N₂O₃Si
• Molecular Weight: 420.668
• Mol file: 708253-91-2.mol

Synonyms:tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate

Chemical Property of tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate

There total 11 articles about tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate 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:

di-tert-butyl dicarbonate (24424-99-5) + (3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-piperidin-3-amine → tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate (708253-91-2)

Guidance literature:

DOI:10.1016/j.bmcl.2004.02.034

Reference yield:

(3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol (161564-09-6) → tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate (708253-91-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: NaN₃ / dimethylformamide / 65 °C

3: H₂ / Ra-Ni

With pyridine; sodium azide; hydrogen; Ra-Ni; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.02.034

Reference yield:

(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin (154343-02-9) → tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate (708253-91-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic anhydride

1.2: diisopropylethylamine

2.1: pyridine

3.1: NaN₃ / dimethylformamide / 65 °C

4.1: H₂ / Ra-Ni

With pyridine; sodium azide; hydrogen; trifluoroacetic anhydride; Ra-Ni; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.02.034

upstream raw materials:

di-tert-butyl dicarbonate

[(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane

(3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol

(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin

Downstream raw materials:

[3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester

(S)-5-amino-3,3-difluoro-piperidine-1-carboxylic acid benzyl ester

benzyl (3S,5R)-3-(tert-butoxycarbonylamino)-5-[tert-butyl(dimethyl)silyl]oxy-piperidine-1-carboxylate

benzyl (3S)-3-(tert-butoxycarbonylamino)-5-oxo-piperidine-1-carboxylate