(3S,5R)-3-(Boc-aMino)-5-Methylpiperidine

Base Information

• Chemical Name: (3S,5R)-3-(Boc-aMino)-5-Methylpiperidine
• CAS No.: 1203651-07-3
• Molecular Formula: C11H22N2O2
• Molecular Weight: 214.308
• Mol file: 1203651-07-3.mol

Synonyms:(3S,5R)-3-(Boc-aMino)-5-Methylpiperidine;tert-butyl N-[(3S,5R)-5-methylpiperidin-3-yl]carbamate;tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate

Chemical Property of (3S,5R)-3-(Boc-aMino)-5-Methylpiperidine

Chemical Property:

• PSA: 50.36000
• LogP: 2.22880
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

97% ^*data from raw suppliers

(3S,5R)-3-(Boc-Amino)-5-methylpiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3S,5R)-3-(Boc-Amino)-5-methylpiperidine is used in the synthetic preparation of pyridinamine compounds as Pim kinase inhibitors, which is useful in the treatment of diseases related to the activity of Pim kinases including, e.g., cancer and other diseases.

Technology Process of (3S,5R)-3-(Boc-aMino)-5-Methylpiperidine

There total 12 articles about (3S,5R)-3-(Boc-aMino)-5-Methylpiperidine 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: 85.8%

tert-butyl [(3S,5R)-1-benzyl-5-methylpiperidin-3-yl]carbamate (1203651-06-2) → tert-butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate (1203651-07-3,1270019-95-8,1187055-56-6,1405128-25-7)

Guidance literature:

With hydrogen; palladium-carbon; In methanol; at 45 ℃; for 36h;

Reference yield:

C18H23N2O2(1+)*Br(1-) → tert-butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate (1203651-07-3,1270019-95-8,1187055-56-6,1405128-25-7) + ((3R,5S)-5-methylpiperidin-3-yl)carbamic acid tert-butyl ester (1270019-92-5,1270019-95-8,1187055-56-6,1405128-25-7)

Guidance literature:

C₁₈H₂₃N₂O₂⁽¹⁺⁾*Br^(1-); With sodium tetrahydroborate; sodium hydroxide; In ethanol; at 0 - 3 ℃; for 3h;

With palladium 10% on activated carbon; hydrogen; In ethanol; for 24h; under 780.078 Torr; Overall yield = 85 %; Overall yield = 0.472 g;

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → tert-butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate (1203651-07-3,1270019-95-8,1187055-56-6,1405128-25-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

1.2: 16 h / -78 - 20 °C

2.1: sodium tetrahydroborate; ethanol / tetrahydrofuran / 16 h / -10 - 20 °C

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 1 h / 0 °C

3.2: 18 h / 70 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol / 15 h / 20 °C / 760.05 Torr

With sodium tetrahydroborate; ethanol; palladium 10% on activated carbon; hydrogen; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

tert-butyl [(3S,5R)-1-benzyl-5-methylpiperidin-3-yl]carbamate

L-Pyroglutamic acid

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

(2S,4R)-1-(tert-butyl) 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

benzyl [2-{[(4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(4-methylpiperazin-1-yl)quinolin-3-yl]carbamate

benzyl (7-bromo-2-{[(4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)amino]carbonyl}quinolin-3-yl)carbamate

benzyl [2-{[(4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-3-yl]carbamate

benzyl [2-{[(4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(2-oxopiperidin-1-yl)quinolin-3-yl]carbamate