2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:382141-43-7
Molecular Formula:C₂₂H₃₁NO₆
Molecular Weight:405.491
Hs Code.:

2-(4-<i>tert</i>-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

Synonyms:2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of 2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of 2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 10 articles about 2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl 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: 62.0%

: 540-88-5
acetic acid tert-butyl ester

: N,N'-carbonyl diimidazole

: 382141-42-6
(S)-2-(2-Carboxy-ethyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

: 382141-43-7
2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: N,N'-carbonyl diimidazole; (S)-2-(2-Carboxy-ethyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester; In tetrahydrofuran; at 20 ℃;

acetic acid tert-butyl ester; With lithium diisopropyl amide; at 0 ℃;
DOI:10.1016/S0040-4039(01)01583-0

Reference yield:

: 32159-21-0
Cbz-L-pGlu-OH

: 382141-43-7
2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / -10 °C

1.2: 61 percent / NaBH₄ / methanol / 0 °C

2.1: 92 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3.1: 93 percent / p-TsOH / 20 °C

4.1: 90 percent / pyridine / 0 °C

5.1: 60 percent / NaI; CaCO₃ / dimethylformamide / 80 °C

6.1: SO₃-pyridine; Et₃N / dimethylsulfoxide / 20 °C

7.1: tetrahydrofuran / 20 °C

8.1: 100 percent / NaBH₄; CuCl / methanol; tetrahydrofuran / 0 °C

9.1: 84 percent / aq. NaOH / methanol / 20 °C

10.1: tetrahydrofuran / 20 °C

10.2: 62 percent / LDA / 0 °C

With 4-methyl-morpholine; pyridine; sodium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; chloroformic acid ethyl ester; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; calcium carbonate; sodium iodide; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 7.1: Wittig reaction;
DOI:10.1016/S0040-4039(01)01583-0

Reference yield:

: 153870-19-0
benzyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate

: 382141-43-7
2-(4-tert-butoxycarbonyl-3-oxo-butyl)-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2.1: 93 percent / p-TsOH / 20 °C

3.1: 90 percent / pyridine / 0 °C

4.1: 60 percent / NaI; CaCO₃ / dimethylformamide / 80 °C

5.1: SO₃-pyridine; Et₃N / dimethylsulfoxide / 20 °C

6.1: tetrahydrofuran / 20 °C

7.1: 100 percent / NaBH₄; CuCl / methanol; tetrahydrofuran / 0 °C

8.1: 84 percent / aq. NaOH / methanol / 20 °C

9.1: tetrahydrofuran / 20 °C

9.2: 62 percent / LDA / 0 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; calcium carbonate; sodium iodide; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 6.1: Wittig reaction;
DOI:10.1016/S0040-4039(01)01583-0