(2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

Base Information

Chemical Name:(2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester
CAS No.:862177-23-9
Molecular Formula:C₃₄H₃₆N₂O₈
Molecular Weight:600.668
Hs Code.:

Synonyms:(2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Chemical Property of (2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Technology Process of (2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

There total 4 articles about (2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl 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: 91.0%

: 862177-22-8
(2S,5S)-5-aminopiperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 862177-23-9
(2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: (2S,5S)-5-aminopiperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester; With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1.5h; Heating;

(fluorenylmethoxy)carbonyl chloride; In dichloromethane; at 0 - 20 ℃; for 40h; 91;
DOI:10.1021/ol0507672

Reference yield:

: 147489-30-3
(2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

: 862177-23-9
(2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: KCN / dimethylformamide; H₂O / 4 h / 60 °C

2.1: 2.6 g / DMAP / tetrahydrofuran / 3 h / 20 °C

3.1: 91 percent / aq. KOH / tetrahydrofuran / 0.5 h / 20 °C

4.1: DIPEA; TMSCl / CH₂Cl₂ / 1.5 h / Heating

4.2: 91 percent / CH₂Cl₂ / 40 h / 0 - 20 °C / 91

With dmap; potassium cyanide; potassium hydroxide; chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Bucherer-Bergs reaction;
DOI:10.1021/ol0507672

Reference yield:

: (8S)-2,4-dioxo-1,3,7-triazaspiro[4.5]decane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester

: 862177-23-9
(2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2.6 g / DMAP / tetrahydrofuran / 3 h / 20 °C

2.1: 91 percent / aq. KOH / tetrahydrofuran / 0.5 h / 20 °C

3.1: DIPEA; TMSCl / CH₂Cl₂ / 1.5 h / Heating

3.2: 91 percent / CH₂Cl₂ / 40 h / 0 - 20 °C / 91

With dmap; potassium hydroxide; chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0507672