tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate
• CAS No.: 176966-86-2
• Molecular Formula: C₂₇H₃₉NO₃Si
• Molecular Weight: 453.697
• Mol file: 176966-86-2.mol

Synonyms:tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate

Chemical Property of tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate

There total 10 articles about tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate 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: 78.0%

(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester (176966-79-3) → tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate (176966-86-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.07.042

Reference yield:

tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2H-2-oxo-5,6-dihydro-piperidine-1-carboxylate (176966-80-6) → tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate (176966-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 12 h / 1500.1 Torr / Ambient temperature

2: 45 percent / BH₃*S(CH₃)2 / tetrahydrofuran / 3 h / 70 °C

With dimethylsulfide borane complex; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/0957-4166(96)00085-7

Reference yield:

(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-3-phenylselanyl-piperidine-1-carboxylic acid tert-butyl ester → tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate (176966-86-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 30percent H₂O₂ / ethyl acetate / 0.75 h / Ambient temperature

2: H₂ / 10percent Pd/C / ethyl acetate / 12 h / 1500.1 Torr / Ambient temperature

3: 45 percent / BH₃*S(CH₃)2 / tetrahydrofuran / 3 h / 70 °C

With dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/0957-4166(96)00085-7

upstream raw materials:

(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

(S)-5-hydroxypiperidin-2-one

tert-butylchlorodiphenylsilane

Downstream raw materials:

tert-butyl (3S,4R)-3-hydroxy-4-methyl-piperidine-1-carboxylate

tasocitinib

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate