(2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Chemical Name:(2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
CAS No.:540508-41-6
Molecular Formula:C₁₉H₂₆N₂O₈
Molecular Weight:410.424
Hs Code.:

Synonyms:(2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Chemical Property of (2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Technology Process of (2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 6 articles about (2S,3R)-3-[4-(1-Hydroxy-2-nitro-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:

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

: 540508-41-6
(2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 6 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

With dmap; sodium hypophosphite; sodium; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; 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

: 540508-41-6
(2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 7 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

With dmap; sodium hypophosphite; dimethylsulfide borane complex; sodium; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; 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

Reference yield:

: 540508-35-8
(2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

: 540508-41-6
(2S,3R)-3-[4-(1-Hydroxy-2-nitro-ethyl)-phenoxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 93 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 °C

3: 93 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

With dmap; sodium hypophosphite; sodium; dicyclohexyl-carbodiimide; nickel; In pyridine; methanol; dichloromethane; water; acetic acid; 3: Henry reaction;
DOI:10.1016/S0040-4039(03)00278-8