tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate
• CAS No.: 774609-73-3
• Molecular Formula: C₁₂H₂₀N₂O₃
• Molecular Weight: 240.302
• Hs Code.: 2933399090
• Mol file: 774609-73-3.mol

Synonyms:tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate

Chemical Property of tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate

Chemical Property:

• Boiling Point: 387.1±27.0 °C(Predicted)
• PKA: 13.45±0.20(Predicted)
• PSA: 73.56000
• Density: 1.138±0.06 g/cm3(Predicted)
• LogP: 1.59998
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate

There total 2 articles about tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-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: 58.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + cyanomethyl bromide (590-17-0) → 4-(cyanomethyl)-4-hydroxypiperidine-1-formic acid tert-butyl ester (774609-73-3)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1.16667h;

N-tert-butyloxycarbonylpiperidin-4-one; cyanomethyl bromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 2h;

Reference yield: 52.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + acetonitrile (75-05-8,26809-02-9) → 4-(cyanomethyl)-4-hydroxypiperidine-1-formic acid tert-butyl ester (774609-73-3)

Guidance literature:

acetonitrile; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

N-tert-butyloxycarbonylpiperidin-4-one; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Inert atmosphere;

Reference yield:

4-(cyanomethyl)-4-hydroxypiperidine-1-formic acid tert-butyl ester (774609-73-3) + di-tert-butyl dicarbonate (24424-99-5) → 2-oxo-1-oxa-3,9-diazaspiro[5.5]undecane-9-formic acid tert-butyl ester (1209319-87-8)

Guidance literature:

With hydrogen; In methanol; at 40 ℃; for 10h; under 2585.81 Torr;

upstream raw materials:

N-tert-butyloxycarbonylpiperidin-4-one

cyanomethyl bromide

acetonitrile

Downstream raw materials:

2-oxo-1-oxa-3,9-diazaspiro[5.5]undecane-9-formic acid tert-butyl ester

Refernces

• 1、 -. "QUINAZOLINE COMPOUND FOR EGFR INHIBITION". Paragraph 0197-0198. . Retrieved 2019/11/21.
• 2、 -. "SUBSTITUTED PYRAZOLO[3,4-b]PYRIDIN-6-CARBOXYLIC ACIDS AND METHOD OF USE". Paragraph 1662; 1663. . Retrieved 2017/05/14.