tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Base Information

Chemical Name:tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate
CAS No.:865704-60-5
Molecular Formula:C₂₀H₂₆N₂O₅
Molecular Weight:374.437
Hs Code.:

Synonyms:tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

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Chemical Property of tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

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Technology Process of tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

There total 10 articles about tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate 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: 75.0%

: 865704-58-1
(3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-{[(tert-butoxycarbonyl)amino]methyl}-4-oxobutanoic acid

: 865704-60-5
tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1055/s-2005-865362

Reference yield:

: 865704-45-6
4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid

: 865704-60-5
tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 50 percent / P₂O₅ / CHCl₃ / 60 h / 20 °C

2.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

3.1: 98 percent / TFA / CH₂Cl₂ / 20 °C

4.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

5.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

6.1: toluene / Heating

7.1: 0.91 g / toluene / Heating

8.1: 97 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

9.1: 75 percent / BH₃*Me₂S / tetrahydrofuran / 3 h / 20 °C

With sodium azide; dimethylsulfide borane complex; hydrogen; sodium hexamethyldisilazane; phosphorus pentoxide; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; toluene; 6.1: Curtius rearrangement;
DOI:10.1055/s-2005-865362

Reference yield:

: 865704-46-7
tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate

: 865704-60-5
tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

2.1: 98 percent / TFA / CH₂Cl₂ / 20 °C

3.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

4.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

5.1: toluene / Heating

6.1: 0.91 g / toluene / Heating

7.1: 97 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

8.1: 75 percent / BH₃*Me₂S / tetrahydrofuran / 3 h / 20 °C

With sodium azide; dimethylsulfide borane complex; hydrogen; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 5.1: Curtius rearrangement;
DOI:10.1055/s-2005-865362