3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Base Information

Chemical Name:3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
CAS No.:540508-43-8
Molecular Formula:C₂₅H₄₂N₂O₆Si
Molecular Weight:494.704
Hs Code.:

3-{4-[2-amino-1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-<i>tert</i>-butyl ester 2-methyl ester

Synonyms:3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Chemical Property of 3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Technology Process of 3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 8 articles about 3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-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: 82.0%

: 540508-63-2
3-{4-[1-(tert-butyl-dimethyl-silanyloxy)-2-nitro-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 540508-43-8
3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: With ammonium formate; palladium on activated charcoal; In methanol; at 0 - 25 ℃; for 4h;
DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

: 128836-20-4
tert-butyl (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-hydroxypyrrolidine-1-carboxylate

: 540508-43-8
3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

2.1: 88 percent / AcOH / tetrahydrofuran; H₂O / 15 h / 40 - 45 °C

3.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C / Swern-Masamune oxidation

3.2: 81 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

4.1: 96 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 93 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 °C

6.1: 93 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

7.1: 93 percent / imidazole / dimethylformamide / 24 h / 0 - 25 °C

8.1: 82 percent / HCO₂NH₄ / Pd/C / methanol / 4 h / 0 - 25 °C

With 1H-imidazole; dmap; sodium hypophosphite; ammonium formate; sodium; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 6.1: Henry reaction;
DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

: 123278-55-7
(4R,5S)-5-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-4-hydroxy-1-<(1,1-dimethylethoxy)carbonyl>-pyrrolidin-2-one

: 540508-43-8
3-{4-[2-amino-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 88 percent / BH₃*SMe₂ / tetrahydrofuran / 5 h / Heating

2.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

3.1: 88 percent / AcOH / tetrahydrofuran; H₂O / 15 h / 40 - 45 °C

4.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C / Swern-Masamune oxidation

4.2: 81 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

5.1: 96 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

6.1: 93 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 °C

7.1: 93 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

8.1: 93 percent / imidazole / dimethylformamide / 24 h / 0 - 25 °C

9.1: 82 percent / HCO₂NH₄ / Pd/C / methanol / 4 h / 0 - 25 °C

With 1H-imidazole; dmap; sodium hypophosphite; dimethylsulfide borane complex; ammonium formate; sodium; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 7.1: Henry reaction;
DOI:10.1016/S0040-4039(03)00278-8