(1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester
CAS No.:544711-78-6
Molecular Formula:C₂₅H₃₉NO₆Si
Molecular Weight:477.673
Hs Code.:

Synonyms:(1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester

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Chemical Property of (1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester

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Technology Process of (1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester

There total 16 articles about (1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl 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: 70.0%

: 544711-77-5
(1R,6R,7aR)-6-(hydroxy)hexahydropyrrolizine-1-carboxylic acid methyl ester

: 544711-79-7
3-{4-[(tert-butyldimethylsilyl)oxy]-3-methoxyphenyl}propanoic acid

: 544711-78-6
(1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester

Guidance literature:: With dmap; dacarbazine; In dichloromethane;
DOI:10.1021/ol034369f

Reference yield:

: 544711-65-1
(4R,5R)-5-(2,3-dihydroxypropyl)-4-[(S)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidin-2-one

: 544711-78-6
(1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: borane-dimethyl sulfide complex / tetrahydrofuran / 5.5 h / Heating

1.2: triethylamine / Pd/C / methanol / 20 °C

1.3: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - 20 °C

2.1: 0.266 g / sodium borohydride / ethanol / 4 h / 0 °C

3.1: 82 percent / imidazole; DMAP / dimethylformamide / 20 °C

4.1: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2.5 h / 20 °C

5.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - 20 °C

6.1: LiHMDS / tetrahydrofuran / 1.5 h / -90 - -65 °C

6.2: 0.046 g / tetrahydrofuran / 2 h / -65 - -50 °C

7.1: 63 percent / P(C₆H₅)3; triethylamine; Pd(OAc)2 / dimethylformamide / 4 h / 40 °C

8.1: 93 percent / H₂ / Pd/C / methanol / 20 °C

9.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

10.1: 70 percent / DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; dmap; palladium diacetate; sodium tetrahydroborate; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.3: Swern oxidation / 5.1: Swern oxidation;
DOI:10.1021/jo050983o

Reference yield:

: 544711-62-8
2-[(S)-1-(pent-4-en-1-ynyloxy)ethyl]-1,3,5-triisopropylbenzene

: 544711-78-6
(1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: borane-dimethyl sulfide complex / tetrahydrofuran / 5.5 h / Heating

1.2: triethylamine / Pd/C / methanol / 20 °C

1.3: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - 20 °C

2.1: 0.266 g / sodium borohydride / ethanol / 4 h / 0 °C

3.1: 82 percent / imidazole; DMAP / dimethylformamide / 20 °C

4.1: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2.5 h / 20 °C

5.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - 20 °C

6.1: LiHMDS / tetrahydrofuran / 1.5 h / -90 - -65 °C

6.2: 0.046 g / tetrahydrofuran / 2 h / -65 - -50 °C

7.1: 63 percent / P(C₆H₅)3; triethylamine; Pd(OAc)2 / dimethylformamide / 4 h / 40 °C

8.1: 93 percent / H₂ / Pd/C / methanol / 20 °C

9.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

10.1: 70 percent / DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; dmap; palladium diacetate; sodium tetrahydroborate; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 2.3: Swern oxidation / 6.1: Swern oxidation;
DOI:10.1021/jo050983o