[4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester

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Chemical Name:[4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester
CAS No.:1260251-23-7
Molecular Formula:C₂₃H₂₃FN₂O₄
Molecular Weight:410.445
Hs Code.:

Synonyms:[4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester

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Chemical Property of [4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester

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Technology Process of [4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester

There total 20 articles about [4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]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: 100.0%

: 1260251-22-6
[2R-(6-fluoro-1H-indol-3-ylmethyl)-4S-hydroxypyrrolidin-1-yl]carboxylic acid benzyl ester

: 108-24-7
acetic anhydride

: 1260251-23-7
[4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester

Guidance literature:: With 4-methyl-morpholine; dmap; In tetrahydrofuran; at 15 - 20 ℃; Inert atmosphere; Large scale;
DOI:10.1021/acs.oprd.5b00390

Reference yield:

: 13504-85-3
(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

: 1260251-23-7
[4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 22 h / 26 °C / Cooling

2.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene / 4 h / 20 °C

3.1: ethylmagnesium bromide / toluene; chlorobenzene; diethyl ether / 1.02 h / -4 - 2.5 °C

3.2: 5.75 h / 2 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 57 h / 20 °C

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 17 h / 2 - 20 °C

6.1: methanol; sodium hydroxide / tetrahydrofuran; water / 2 h

7.1: lithium borohydride / tetrahydrofuran / 2.61 h

7.2: 16 h

8.1: dmap / dichloromethane / 16 h / 20 °C

With methanol; dmap; lithium borohydride; oxalyl dichloride; di-isopropyl azodicarboxylate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; chlorobenzene; toluene;

Reference yield:

: 81396-84-1
(2S,4R)-1-((benzyloxy)carbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid

: 1260251-23-7
[4S-acetoxy-2R-(6-fluoro-1H-indol-3-ylmethyl)pyrrolidin-1-yl]carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene / 4 h / 20 °C

2.1: ethylmagnesium bromide / toluene; chlorobenzene; diethyl ether / 1.02 h / -4 - 2.5 °C

2.2: 5.75 h / 2 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 57 h / 20 °C

4.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 17 h / 2 - 20 °C

5.1: methanol; sodium hydroxide / tetrahydrofuran; water / 2 h

6.1: lithium borohydride / tetrahydrofuran / 2.61 h

6.2: 16 h

7.1: dmap / dichloromethane / 16 h / 20 °C

With methanol; dmap; lithium borohydride; oxalyl dichloride; di-isopropyl azodicarboxylate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; chlorobenzene; toluene;