1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, hydrochloride (1:1), (3R,4S)-

Base Information

• Chemical Name: 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, hydrochloride (1:1), (3R,4S)-
• CAS No.: 267230-41-1
• Molecular Formula: C₂₀H₃₀N₂O₄*ClH
• Molecular Weight: 398.93
• Mol file: 267230-41-1.mol

Synonyms:1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]amino]-, 1-(1,1-dimethylethyl) 3-ethyl ester, hydrochloride (1:1), (3R,4S)-;

Chemical Property of 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, hydrochloride (1:1), (3R,4S)-

Chemical Property:

• PSA: 67.87000
• LogP: 4.26660

Purity/Quality:

99% ^*data from raw suppliers

1,3-Pyrrolidinedicarboxylicacid,4-[[(1R)-1-phenylethyl]amino]-,1-(1,1-dimethylethyl)3-ethylester,hydrochloride(1:1),(3R,4S)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, hydrochloride (1:1), (3R,4S)-

There total 10 articles about 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, hydrochloride (1:1), (3R,4S)- 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: 25.0%

(R)-1-phenyl-ethyl-amine (3886-69-9) + 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (146256-98-6) → (3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride (346610-81-9,267230-41-1)

Guidance literature:

(R)-1-phenyl-ethyl-amine; 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester; With acetic acid; In ethanol; at 20 ℃; for 4h;

With sodium cyanoborohydride; In ethanol; at 75 ℃; for 16h;

With hydrogenchloride; In 1,4-dioxane; ethyl acetate; at 0 ℃; for 3h;

DOI:10.1021/ja0614565

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride (346610-81-9,267230-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / NaHCO₃ / acetonitrile / 16 h / 20 °C

2.1: NaH / toluene / 1 h / 20 °C

2.2: 62 percent / toluene / 4.5 h / 0 °C

3.1: AcOH / ethanol / 4 h / 20 °C

3.2: NaCNBH₃ / ethanol / 16 h / 75 °C

3.3: 25 percent / HCl / ethyl acetate; dioxane / 3 h / 0 °C

With sodium hydride; sodium hydrogencarbonate; acetic acid; In ethanol; toluene; acetonitrile;

DOI:10.1021/ja0614565

Reference yield:

ethyl 2-(tert-butoxycarbonylamino)acetate (14719-37-0) → (3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride (346610-81-9,267230-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / toluene / 1 h / 20 °C

1.2: 62 percent / toluene / 4.5 h / 0 °C

2.1: AcOH / ethanol / 4 h / 20 °C

2.2: NaCNBH₃ / ethanol / 16 h / 75 °C

2.3: 25 percent / HCl / ethyl acetate; dioxane / 3 h / 0 °C

With sodium hydride; acetic acid; In ethanol; toluene;

DOI:10.1021/ja0614565

upstream raw materials:

(R)-1-phenyl-ethyl-amine

4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

di-tert-butyl dicarbonate

ethyl 2-(tert-butoxycarbonylamino)acetate

Refernces

• 1、 Reenabthue, Nisanath,Boonlua, Chalothorn,Vilaivan, Chotima,Vilaivan, Tirayut,Suparpprom, Chaturong. "3-Aminopyrrolidine-4-carboxylic acid as versatile handle for internal labeling of pyrrolidinyl PNA". . p. 6465 - 6469. Retrieved 2011/12/02.