1-Pyrrolidinecarboxylic acid, 2-[[[(4-nitrophenoxy)carbonyl]amino]methyl]-, 9H-fluoren-9-ylmethyl ester, (2S)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-[[[(4-nitrophenoxy)carbonyl]amino]methyl]-, 9H-fluoren-9-ylmethyl ester, (2S)-
• CAS No.: 391624-45-6
• Molecular Formula: C₂₇H₂₅N₃O₆
• Molecular Weight: 487.512
• Mol file: 391624-45-6.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[[[(4-nitrophenoxy)carbonyl]amino]methyl]-, 9H-fluoren-9-ylmethyl ester, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[[[(4-nitrophenoxy)carbonyl]amino]methyl]-, 9H-fluoren-9-ylmethyl ester, (2S)-

There total 4 articles about 1-Pyrrolidinecarboxylic acid, 2-[[[(4-nitrophenoxy)carbonyl]amino]methyl]-, 9H-fluoren-9-ylmethyl ester, (2S)- 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:

Fmoc-Pro-OH (71989-31-6) → 2-[(4-nitro-phenoxycarbonylamino)-methyl]-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (391624-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NMM; ICF / 1,2-dimethoxy-ethane / 1 h / -15 °C

1.2: 80 percent / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / -15 °C

2.1: 92 percent / DEAD; PPh₃; HN₃ / benzene / 20 °C

3.1: H₂ / 10percent Pd/C / tetrahydrofuran; CHCl₃ / 20 °C

4.1: 2.08 g / DiPEA / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; tris-(2-chloro-ethyl)-amine; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; 10percent Pd/C; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; benzene; 2.1: Mitsunobu reaction;

DOI:10.1021/jo010656q

Reference yield:

(S)-(9H-fluoren-9-yl)methyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (148625-77-8) → 2-[(4-nitro-phenoxycarbonylamino)-methyl]-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (391624-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / DEAD; PPh₃; HN₃ / benzene / 20 °C

2: H₂ / 10percent Pd/C / tetrahydrofuran; CHCl₃ / 20 °C

3: 2.08 g / DiPEA / CH₂Cl₂ / 0 - 20 °C

With tris-(2-chloro-ethyl)-amine; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; 10percent Pd/C; In tetrahydrofuran; dichloromethane; chloroform; benzene; 1: Mitsunobu reaction;

DOI:10.1021/jo010656q

Reference yield:

2-azidomethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (391624-35-4) → 2-[(4-nitro-phenoxycarbonylamino)-methyl]-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (391624-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran; CHCl₃ / 20 °C

2: 2.08 g / DiPEA / CH₂Cl₂ / 0 - 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1021/jo010656q

upstream raw materials:

4-Nitrophenyl chloroformate

Fmoc-Pro-OH

(S)-(9H-fluoren-9-yl)methyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

2-azidomethyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Refernces