(2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:531539-31-8
Molecular Formula:C₂₈H₂₇NO₆
Molecular Weight:473.525
Hs Code.:

Synonyms:(2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 7 articles about (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-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: 55.0%

: 703-55-9
1-naphthylmagnesiumbromide

: 531539-23-8
(2S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

: 531539-31-8
(2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether; at -78 - -20 ℃;
DOI:10.1016/S0040-4020(02)01490-4

Reference yield:

: 3143-02-0
3-hydroxymethyl-3-methyloxethane

: 531539-31-8
(2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: 1,4-diazabicyclooctane; butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 39 percent / tetrahydrofuran / -78 - 20 °C

3.1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

4.1: HMDS; butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

4.2: phenylselenenyl chloride / tetrahydrofuran / -78 - 20 °C

4.3: 48 percent / 1,4-diazabicyclooctane; m-chloroperbenzoic acid / tetrahydrofuran; CH₂Cl₂ / -20 - 20 °C

5.1: 55 percent / CuBr*S(CH₃)2; trimethylsilyl chloride / diethyl ether; tetrahydrofuran / -78 - -20 °C

With dmap; n-butyllithium; chloro-trimethyl-silane; 1,4-diazabicyclooctane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/S0040-4020(02)01490-4

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 531539-31-8
(2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1,4-diazabicyclooctane; butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 39 percent / tetrahydrofuran / -78 - 20 °C

2.1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

3.1: HMDS; butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

3.2: phenylselenenyl chloride / tetrahydrofuran / -78 - 20 °C

3.3: 48 percent / 1,4-diazabicyclooctane; m-chloroperbenzoic acid / tetrahydrofuran; CH₂Cl₂ / -20 - 20 °C

4.1: 55 percent / CuBr*S(CH₃)2; trimethylsilyl chloride / diethyl ether; tetrahydrofuran / -78 - -20 °C

With n-butyllithium; chloro-trimethyl-silane; 1,4-diazabicyclooctane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/S0040-4020(02)01490-4