N-Cbz-3(R)-fluoropyrrolidine

Base Information

• Chemical Name: N-Cbz-3(R)-fluoropyrrolidine
• CAS No.: 163457-21-4
• Molecular Formula: C12H14 F N O2
• Molecular Weight: 223.24300
• Mol file: 163457-21-4.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 3-fluoro-, phenylmethyl ester, (R)-

Chemical Property of N-Cbz-3(R)-fluoropyrrolidine

Chemical Property:

• Boiling Point: 326.3±42.0 °C(Predicted)
• PKA: -3.65±0.40(Predicted)
• PSA: 29.54000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 2.30490

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Cbz-3(R)-fluoropyrrolidine

There total 4 articles about N-Cbz-3(R)-fluoropyrrolidine 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%

(S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester (100858-32-0) → (R)-benzyl 3-fluoropyrrolidine-1-carboxylate (163457-21-4)

Guidance literature:

With N-tosyl-4-chlorobenzenesulfonimidoyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃; for 0.5h; enantiospecific reaction; Sealed tube;

DOI:10.1002/chem.201901176

Reference yield:

(3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (100858-33-1) → (R)-benzyl 3-fluoropyrrolidine-1-carboxylate (163457-21-4)

Guidance literature:

Multi-step reaction with 3 steps

1: DEAD; Ph₃P / toluene

2: aq. KOH / ethanol

3: DAST / CH₂Cl₂ / -78 - 20 °C

With potassium hydroxide; triphenylphosphine; 4,4'-diaminostilbene-2,2'-disulfonic acid; diethylazodicarboxylate; In ethanol; dichloromethane; toluene; 1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2003.12.040

Reference yield:

(S)-benzyl 3-acetoxypyrrolidine-1-carboxylate (130403-93-9) → (R)-benzyl 3-fluoropyrrolidine-1-carboxylate (163457-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. KOH / ethanol

2: DAST / CH₂Cl₂ / -78 - 20 °C

With potassium hydroxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In ethanol; dichloromethane;

DOI:10.1016/j.bmcl.2003.12.040

upstream raw materials:

(S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester

(3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

(S)-benzyl 3-acetoxypyrrolidine-1-carboxylate

Downstream raw materials:

(3R)-3-fluoropyrrolidine

Refernces

• 1、 -. "CYCLOHEXYLALANINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES". Page/Page column 51. . Retrieved 2010/02/15.
• 2、 Caldwell, Charles G.,Chen, Ping,He, Jiafang,Parmee, Emma R.,Leiting, Barbara,Marsilio, Frank,Patel, Reshma A.,Wu, Joseph K.,Eiermann, George J.,Petrov, Aleksandr,He, Huaibing,Lyons, Kathryn A.,Thornberry, Nancy A.,Weber, Ann E.. "Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors". . p. 1265 - 1268. Retrieved 2007/10/03.