Methyl 1-Boc-3-allylpiperidine-3-carboxylate

Base Information

• Chemical Name: Methyl 1-Boc-3-allylpiperidine-3-carboxylate
• CAS No.: 1349644-17-2
• Molecular Formula: C₁₅H₂₅NO₄
• Molecular Weight: 283.368
• Hs Code.: 2933399090
• Mol file: 1349644-17-2.mol

Synonyms:Methyl 1-Boc-3-allylpiperidine-3-carboxylate;1-tert-butyl 3-methyl 3-(prop-2-en-1-yl)piperidine-1,3-dicarboxylate;1-tert-Butyl 3-methyl 3-allylpiperidine-1,3-dicarboxylate

Chemical Property of Methyl 1-Boc-3-allylpiperidine-3-carboxylate

Chemical Property:

• PSA: 55.84000
• LogP: 2.69070

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl1-Boc-3-allylpiperidine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 1-Boc-3-allylpiperidine-3-carboxylate

There total 2 articles about Methyl 1-Boc-3-allylpiperidine-3-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: 94.0%

allyl bromide (106-95-6) + 1-(tert-butyl) 3-methyl piperidine-1,3-dicarboxylate (148763-41-1) → 1-(1,1-dimethylethyl)-3-methyl-3-(2-propen-1-yl)-1,3-piperidinedicarboxylate (1349644-17-2)

Guidance literature:

1-(tert-butyl) 3-methyl piperidine-1,3-dicarboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 1.25h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; hexane; at -78 ℃; for 5h;

Reference yield:

N-(tert-butyloxycarbonyl)nipecotic acid (71381-75-4,88495-54-9,84358-12-3) → 1-(1,1-dimethylethyl)-3-methyl-3-(2-propen-1-yl)-1,3-piperidinedicarboxylate (1349644-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: K₂CO₃ / 20 °C

2.1: LDA / tetrahydrofuran / -78 °C

2.2: tetrahydrofuran

With potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield:

1-(1,1-dimethylethyl)-3-methyl-3-(2-propen-1-yl)-1,3-piperidinedicarboxylate (1349644-17-2) → 7-{[4-(trifluoromethyl)phenyl]sulfonyl}-2-oxa-7-azaspiro[4.5]decan-1-one (1349643-97-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ozone; oxygen / dichloromethane; methanol / 2.17 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Cooling with ice-water bath

1.3: 20 °C / Cooling

2.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Cooling with ice-water bath

2.2: pH 9

3.1: triethylamine / dichloromethane / 21 °C

With oxygen; ozone; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;

upstream raw materials:

allyl bromide

1-(tert-butyl) 3-methyl piperidine-1,3-dicarboxylate

N-(tert-butyloxycarbonyl)nipecotic acid

Downstream raw materials:

(RS)-1,1-dimethylethyl 2-oxa-1-oxo-7-azaspiro[4,5]decan-7-carboxylate

7-{[4-(trifluoromethyl)phenyl]sulfonyl}-2-oxa-7-azaspiro[4.5]decan-1-one

7-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)-2-oxa-7-azaspiro[4.5]decan-1-one

Refernces

• 1、 -. "SPIROCYCLIC DERIVATIVES WITH AFFINITY FOR CALCIUM CHANNELS". Page/Page column 20. . Retrieved 2011/12/02.