methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate

Base Information

Chemical Name:methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate
CAS No.:1365177-48-5
Molecular Formula:C₂₅H₂₈ClNO₄
Molecular Weight:441.955
Hs Code.:

Synonyms:methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate

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Chemical Property of methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate

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Technology Process of methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate

There total 7 articles about methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate 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: 34.0%

: 1365177-51-0
methyl [3-(2-bromoethyl)phenyl]acetate

: 1365177-44-1
ethyl (4R,5E,7S)-4-amino-8-(3-chlorophenyl)-7-hydroxy-5-octenoate trifluoroacetate

: 1365177-48-5
methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 90 ℃; for 8h;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

: 494224-49-6
(R)-ethyl 4-(tert-butoxycarbonylamino)-5-oxopentanoate

: 1365177-48-5
methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C

2.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

3.1: dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 8 h / 90 °C

With borane-THF; sodium hydride; sodium hydrogencarbonate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

: 597577-78-1
(4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester

: 1365177-48-5
methyl [3-(2-{(2R)-2-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxy-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)phenyl]acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -70 - -40 °C

1.2: 0.5 h / -40 - -5 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 20 °C

3.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

4.1: dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 8 h / 90 °C

With borane-THF; oxalyl dichloride; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018