(Z)-tert-butyl 3-(2-Methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (Z)-tert-butyl 3-(2-Methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate
• CAS No.: 441773-67-7
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.28356
• Mol file: 441773-67-7.mol

Synonyms:(Z)-tert-butyl 3-(2-Methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate;tert-butyl 3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

Chemical Property of (Z)-tert-butyl 3-(2-Methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

Chemical Property:

• PSA: 55.84000
• LogP: 1.66450

Purity/Quality:

95+% ^*data from raw suppliers

(Z)-tert-Butyl3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-tert-butyl 3-(2-Methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

There total 2 articles about (Z)-tert-butyl 3-(2-Methoxy-2-oxoethylidene)pyrrolidine-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: 100.0%

trimethyl phosphonoacetate (5927-18-4) + 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (101385-93-7) → tert-butyl 3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate (441773-67-7)

Guidance literature:

trimethyl phosphonoacetate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.333333h;

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 16h;

Reference yield:

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (101385-93-7) → tert-butyl 3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate (441773-67-7)

Guidance literature:

In toluene; at 110 ℃;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield:

tert-butyl 3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate (441773-67-7) → {3-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-pyrrolidin-3-yl}-acetic acid

Guidance literature:

Multi-step reaction with 9 steps

1.1: DIBAL / tetrahydrofuran / -78 °C

2.1: propionic acid / 180 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: P(OMe)3 / CH₂Cl₂ / 20 °C

4.1: NaBH₄ / ethanol / 20 °C

5.1: DIEA / CH₂Cl₂ / 0 °C

6.1: NaH / dimethylformamide / 0 °C

7.1: Oxone / methanol; H₂O

8.1: K₂CO₃ / dimethylformamide

9.1: TFA / CH₂Cl₂

With Oxone; sodium tetrahydroborate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; propionic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Claisen rearrangement;

DOI:10.1016/j.bmcl.2004.06.049

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

trimethyl phosphonoacetate

Downstream raw materials:

3-(2-hydroxy-ethylidene)-pyrrolidine-1-carboxylic acid tert-butyl ester

3-ethoxycarbonylmethyl-3-(4-hydroxy-phenylsulfanylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "CYANOPYRROLIDINE DERIVATIVES WITH ACTIVITY AS INHIBITORS OF USP30". Page/Page column 58-59. . Retrieved 2018/06/16.