(1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

Base Information

Chemical Name:(1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester
CAS No.:566202-74-2
Molecular Formula:C₂₉H₂₈BrNO₅
Molecular Weight:550.449
Hs Code.:

Synonyms:(1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

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Chemical Property of (1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

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Technology Process of (1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

There total 12 articles about (1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl 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:

: 566202-73-1
[2-(4-Benzyloxy-benzyloxy)-5-bromo-phenyl]-diazo-acetic acid (R)-1-methyl-2-oxo-2-pyrrolidin-1-yl-ethyl ester

: (2S,3S)-2-(4-Benzyloxy-phenyl)-5-bromo-2,3-dihydro-benzofuran-3-carboxylic acid (R)-1-methyl-2-oxo-2-pyrrolidin-1-yl-ethyl ester

: 566202-74-2
(1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

Guidance literature:: With Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; In dichloromethane; at 0 ℃; for 0.5h; Title compound not separated from byproducts;
DOI:10.1021/ja036011k

Reference yield:

: 836-43-1
4-benzyloxybenzyl alcohol

: 566202-74-2
(1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 98 percent / SOCl₂

2.1: 95 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

3.1: O₃ / CH₂Cl₂; methanol / 7.5 h / -78 °C

3.2: Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

4.1: 137 g / 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 84 h / 20 °C

5.1: 80 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

6.1: p-acetamidobenzenesulfonyl azide; DBU / acetonitrile / 0 - 20 °C

7.1: 5.10 g / Rh₂(S-DOSP)4 / CH₂Cl₂ / 0.5 h / 0 °C

With sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 4-acetamidobenzenesulfonyl azide; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 5.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2004.06.144

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 566202-74-2
(1'R,2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / NaBH₄ / tetrahydrofuran; H₂O

2.1: 98 percent / SOCl₂

3.1: 95 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

4.1: O₃ / CH₂Cl₂; methanol / 7.5 h / -78 °C

4.2: Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

5.1: 137 g / 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 84 h / 20 °C

6.1: 80 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

7.1: p-acetamidobenzenesulfonyl azide; DBU / acetonitrile / 0 - 20 °C

8.1: 5.10 g / Rh₂(S-DOSP)4 / CH₂Cl₂ / 0.5 h / 0 °C

With sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 4-acetamidobenzenesulfonyl azide; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 6.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2004.06.144