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inquiry(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; methanol | 95% |
With lithium hydroxide In ethanol Reflux; |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With palladium on activated charcoal In methanol at 20℃; for 5h; | 95% |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol at 50℃; under 7600.51 Torr; for 6h; Temperature; | 92.3% |
With sulfuric acid; palladium 10% on activated carbon; hydrogen at 40℃; for 30h; | 80.6% |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 18h; | 92% |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 80℃; under 30003 Torr; for 24h; | 89% |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; Reagent/catalyst; Solvent; | 88% |
4-bromo-1,1'-biphenyl
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3R,5S)-5-(iodomethyl)-3-methyl-2-pyrrolidinone With chloro-trimethyl-silane; ethylene dibromide; zinc In N,N-dimethyl acetamide at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: 4-bromo-1,1'-biphenyl With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 5℃; for 24h; Negishi Coupling; | 87.8% |
4-biphenylylmagnesium bromide
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With copper(l) cyanide In tetrahydrofuran at -30 - 20℃; Inert atmosphere; | 82.3% |
4-bromo-1,1'-biphenyl
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl With iodine; magnesium In tetrahydrofuran at 0 - 60℃; Inert atmosphere; Stage #2: (3R,5S)-5-(bromomethyl)-3-methyl-2-pyrrolidone With iron(III)-acetylacetonate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 82% |
C7H13NO4S
4-biphenylboronic acid
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; dimethyl sulfoxide at 80℃; for 10h; Reagent/catalyst; Solvent; Inert atmosphere; | 82% |
4-bromo-1,1'-biphenyl
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl With iodine; magnesium In tetrahydrofuran at 0 - 60℃; Inert atmosphere; Stage #2: (3R,5S)-5-(tosyloxymethyl)-3-methyl-2-pyrrolidone With iron(III)-acetylacetonate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 74% |
(2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In ethyl acetate at 40℃; Reagent/catalyst; | 72% |
With methanol; potassium hydroxide at 60 - 65℃; for 4h; | 49.3% |
methyl chloroformate
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: ethyl 5-ambo-(2R,4S)-5-([1,1 '-biphenyl]-4-yl)-4-{[(tertbutoxy)carbonyl]amino}-5-hydroxy-2-ethypentanoate; methyl chloroformate In Isopropyl acetate at 0 - 20℃; for 0.0833333h; Stage #2: With 2-methylbutan-2-ol (lithium salt) In n-heptane; Isopropyl acetate at 0 - 2℃; for 3h; | 66% |
(S)-5-biphenyl-4-ylmethylpyrrolidin-2-one
methyl iodide
A
(3S,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one
B
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-5-biphenyl-4-ylmethylpyrrolidin-2-one With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Heating / reflux; Stage #2: methyl iodide In tetrahydrofuran; cyclohexane at -78℃; for 2h; Product distribution / selectivity; |
ethyl (2S,4S)-4-amino-5-[(1,1'-biphenyl)-4-yl]-2-methylpentanoate hydrochloride
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride
A
(3S,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one
B
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: ethyl (2S,4S)-4-amino-5-[(1,1'-biphenyl)-4-yl]-2-methylpentanoate hydrochloride; (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride With triethylamine In Isopropyl acetate at 55℃; for 1h; Stage #2: In Isopropyl acetate for 24h; Product distribution / selectivity; Heating / reflux; |
(3R,5R)-5-(biphenyl-4-yl)methyl-3-methyl-2-oxopyrrolidine-3-carboxylic acid
(3S,5R)-5-biphenyl-4-ylmethyl-3-methyl-2-oxopyrrolidine-3-carboxylic acid
A
(3S,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one
B
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
In toluene for 16h; Product distribution / selectivity; Heating / reflux; |
(3R,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 1h; Product distribution / selectivity; Heating / reflux; |
(3R/S,5S)-5-biphenyl-4-ylmethyl-3-iodomethyl-pyrrolidin-2-one
A
(3S,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one
B
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With hydrogen; triethylamine; palladium on activated charcoal In ethanol at 20℃; under 750.075 Torr; | A n/a B n/a |
4-biphenylylmagnesium bromide
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 4-biphenylylmagnesium bromide With zinc(II) chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: (3R,5S)-5-(bromomethyl)-3-methyl-2-pyrrolidone With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 0 - 20℃; Negishi Coupling; | 0.32 g |
4-biphenylylmagnesium bromide
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
With copper(II) sulfate In tetrahydrofuran at -5 - 20℃; for 48h; Inert atmosphere; | 1.82 g |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 5 - 20 °C 2: copper(l) cyanide / tetrahydrofuran / -30 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 5 - 20 °C 2.1: sodium iodide / acetone / 24 h / Reflux 3.1: ethylene dibromide; zinc; chloro-trimethyl-silane / N,N-dimethyl acetamide / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 24 h / 5 °C View Scheme | |
Multi-step reaction with 3 steps 1: dmap; triethylamine / dichloromethane / 5 - 20 °C 2: sodium iodide / acetone / 24 h / Reflux 3: copper(II) sulfate / tetrahydrofuran / 48 h / -5 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: triphenylphosphine; bromine / dichloromethane / 0 - 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium iodide / acetone / 24 h / Reflux 2.1: ethylene dibromide; zinc; chloro-trimethyl-silane / N,N-dimethyl acetamide / 1 h / 0 - 5 °C / Inert atmosphere 2.2: 24 h / 5 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium iodide / acetone / 24 h / Reflux 2: copper(II) sulfate / tetrahydrofuran / 48 h / -5 - 20 °C / Inert atmosphere View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere 2: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 3: thionyl chloride / 7 h / 20 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C View Scheme |
(2R,4R)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentane-1,2-diol
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Nonafluorobutanesulfonyl fluoride / dichloromethane / 3 h / 0 °C / Inert atmosphere 2.1: magnesium; iodine / tetrahydrofuran / Heating; Inert atmosphere 2.2: 0.5 h / 0 °C 2.3: 0 - 20 °C 3.1: dmap; triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere 5.1: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 6.1: thionyl chloride / 7 h / 20 °C / Inert atmosphere 7.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 7 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: magnesium; iodine / tetrahydrofuran / Heating; Inert atmosphere 1.2: 0.5 h / 0 °C 1.3: 0 - 20 °C 2.1: dmap; triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere 3.1: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere 4.1: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 5.1: thionyl chloride / 7 h / 20 °C / Inert atmosphere 6.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: dmap; triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere 2: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere 3: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 4: thionyl chloride / 7 h / 20 °C / Inert atmosphere 5: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere 2: thionyl chloride / 7 h / 20 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 20 °C View Scheme |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: toluene / 36 h / 40 - 50 °C 2.1: ethyl bromide; magnesium / tetrahydrofuran / 20 °C / Inert atmosphere 2.2: -78 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C View Scheme |
(4S,1'R)-4,5-dihydro-2-(1-methyl-3-butenyl)-4-(1-methylethyl)oxazole
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: water; hydrogenchloride / 3 h / 0 - 5 °C / Inert atmosphere 2.1: ozone / dichloromethane / 0.25 h / -78 - 20 °C 3.1: toluene / 36 h / 40 - 50 °C 4.1: ethyl bromide; magnesium / tetrahydrofuran / 20 °C / Inert atmosphere 4.2: -78 °C 5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C View Scheme |
ethanol
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester sulfuric acid salt
Conditions | Yield |
---|---|
With sulfuric acid at 75 - 85℃; for 16h; Reagent/catalyst; | 88.2% |
With sulfuric acid at 80 - 120℃; for 24h; Product distribution / selectivity; |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 16h; Time; Reflux; | 85.6% |
With hydrogenchloride In methanol at 70 - 85℃; for 24h; | 82% |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid for 20h; Reflux; | 80% |
With hydrogenchloride; acetic acid In water for 20h; Heating / reflux; |
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane; N,N-dimethyl-formamide at -15 - 0℃; Inert atmosphere; | 68% |
pyrrolidine
formaldehyd
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
(3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-1-pyrrolidin-1-ylmethylpyrrolidin-2-one
Conditions | Yield |
---|---|
In ethanol; water for 3h; Product distribution / selectivity; Heating / reflux; |
(3S,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
pivaloyl chloride
A
(3R,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one
B
(3S,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3S,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one; (3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: pivaloyl chloride at -78 - 20℃; for 4h; Product distribution / selectivity; |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
pivaloyl chloride
(3R,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: (3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: pivaloyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Product distribution / selectivity; |
ethanol
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water at 80 - 120℃; for 24h; Product distribution / selectivity; |
ethanol
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
(2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester (p-toluenesulphonate salt)
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 80 - 120℃; for 24h; Product distribution / selectivity; |
(3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one
di-tert-butyl dicarbonate
(3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap; triethylamine In ethyl acetate at 50℃; for 1h; Product distribution / selectivity; | |
Stage #1: (3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one With dmap at 20℃; Stage #2: di-tert-butyl dicarbonate With triethylamine |
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