3-BENZYL-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-ETHYL ESTER

Base Information

• Chemical Name: 3-BENZYL-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-ETHYL ESTER
• CAS No.: 170842-80-5
• Molecular Formula: C20H29NO4
• Molecular Weight: 347.455
• Hs Code.: 2933399090
• Mol file: 170842-80-5.mol

Synonyms:1-tert-Butyl 3-ethyl 3-benzylpiperidine-1,3-dicarboxylate;S-3-Carbethoxy-3-benzyl-N-Boc-piperidine;(+/-)-N-(t-butoxycarbonyl)-3-(carboethoxy)-3-(phenylmethyl)-piperidine;3-Benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester;

Chemical Property of 3-BENZYL-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-ETHYL ESTER

Chemical Property:

• Boiling Point: 431.8±38.0 °C(Predicted)
• PKA: -2.40±0.40(Predicted)
• PSA: 55.84000
• Density: 1.101±0.06 g/cm3(Predicted)
• LogP: 3.74740
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

1-tert-Butyl3-Ethyl3-Benzylpiperidine-1,3-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-BENZYL-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-ETHYL ESTER

There total 5 articles about 3-BENZYL-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-ETHYL ESTER 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:

ethyl N-(t-butyloxycarbonyl)nipecotate (148672-74-6,130250-54-3) + benzyl bromide (100-39-0) → 3-Benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (170842-80-5)

Guidance literature:

With lithium hexamethyldisilazane; Multistep reaction; 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 0 deg C;

DOI:10.1021/jm9800191

Reference yield:

(42/58) MeCN + (42/58→62/38) MeCN + (62/38) MeCN + S-3-Carbethoxy-3-benzyl-2-hydroxy-N-Boc-piperidine + phosphoric acid (86119-84-8,7664-38-2) + boron trifluoride (7637-07-2) + tert-butyl nitrosoformate (121893-20-7) → 3-Benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (170842-80-5)

Guidance literature:

With triethylsilane; trifluoroborane diethyl ether; In dichloromethane;

Reference yield:

ethyl N-(t-butyloxycarbonyl)nipecotate (148672-74-6,130250-54-3) + benzyl bromide (100-39-0) + lithium diisopropyl amide (4111-54-0) → 3-Benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (170842-80-5)

Guidance literature:

In tetrahydrofuran;

upstream raw materials:

ethyl N-(t-butyloxycarbonyl)nipecotate

benzyl bromide

di-tert-butyl dicarbonate

Ethyl nipecotate

Downstream raw materials:

(+/-)-N-(t-butoxycarbonyl)-3-(hydroxymethyl)-3-(phenylmethyl)-piperidine

(S)-3-Benzyl-1-[(R)-2-(2-tert-butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionyl]-piperidine-3-carboxylic acid ethyl ester

(S)-3-Benzyl-1-[(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-3-carboxylic acid ethyl ester

(S)-3-carbethoxy-3-benzylpiperidine

Refernces

• 1、 -. "Compound with growth hormone releasing properties". . . Retrieved 2008/06/13.
• 2、 Yang, Lihu,Morriello, Greg,Patchett, Arthur A.,Leung, Kwan,Jacks, Tom,Cheng, Kang,Schleim, Klaus D.,Feeney, William,Chan, Wanda W.-S.,Chiu, Shuet-Hing L.,Smith, Roy G.. "1-[2(R)-(2-amino-2-methylpropionyl-amino)-3-(1H-indol-3-yl)propionyl]- 3-benzylpiperidine-3(S)-carboxylic acid ethyl ester (L-163,540): A potent, orally bioavailable, and short-duration growth hormone secretagogue [1]". . p. 2439 - 2441. Retrieved 2007/10/03.