(4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate

Base Information

Chemical Name:(4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate
CAS No.:221072-60-2
Molecular Formula:C₁₉H₂₇NO₅
Molecular Weight:349.427
Hs Code.:

Synonyms:(4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate

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Chemical Property of (4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate

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Technology Process of (4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate

There total 5 articles about (4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate 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: 49.0%

: 27374-25-0
[(1-Ethoxycyclopropyl)oxy]trimethylsilane

: 111491-98-6
(2S)-2-Acetyl-N-(benzyloxycarbonyl)pyrrolidine

: 221072-60-2
(4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate

Guidance literature:: [(1-Ethoxycyclopropyl)oxy]trimethylsilane; With titanium tetrachloride; In dichloromethane; at 21 ℃;

(2S)-2-Acetyl-N-(benzyloxycarbonyl)pyrrolidine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo9820972

Reference yield:

: 5211-23-4
N-carbobenzyloxy-L-proline methyl ester

: 221072-60-2
(4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 17 percent / tetrahydrofuran; toluene / 0 - 20 °C

2.1: TiCl₄ / CH₂Cl₂ / 21 °C

2.2: 49 percent / CH₂Cl₂ / -78 - 20 °C

With titanium tetrachloride; In tetrahydrofuran; dichloromethane; toluene; 1.1: Condensation / 2.1: Metallation / 2.2: Addition;
DOI:10.1021/jo9820972

Reference yield:

: 71461-30-8
(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester

: 221072-60-2
(4S)-ethyl 4-[1-[(benzyloxy)carbonyl]-2S-pyrrolidinyl]-4-hydroxypentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 61 percent / diethyl ether; tetrahydrofuran / 1.5 h / -78 - 0 °C

2.1: 91 percent / Jones reagent / acetone / 0.5 h / 0 - 20 °C

3.1: TiCl₄ / CH₂Cl₂ / 21 °C

3.2: 49 percent / CH₂Cl₂ / -78 - 20 °C

With jones reagent; titanium tetrachloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 1.1: Grignard reaction / 2.1: Oxidation / 3.1: Metallation / 3.2: Addition;
DOI:10.1021/jo9820972