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inquirypara-methylacetophenone
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
With formate dehydrogenase; Arthrobacter citreus S9 ω-transaminase; ATA-113 ω-transaminase; sodium formate; isopropylamine; NADH; yeast alcohol dehydrogenase pH=7; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; | 99% |
Stage #1: para-methylacetophenone With ochrobactrum anthropi ω-transaminases W58L/R417A; isopropylamine In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 460 Torr; for 8h; pH=7; Enzymatic reaction; Stage #2: With hydrogenchloride; perchloric acid In water; acetonitrile | 92% |
With pyridoxal 5'-phosphate; ω-transaminases from ochrobactrum anthropi mutant W58A; isopropylamine In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 300 Torr; for 7h; pH=7; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | n/a |
(1R)-2-({[(1S)-1-(4-methylphenyl)ethyl]amino}oxy)-1-phenylethanol
A
(R)-1-phenyl-1,2-ethanediol
B
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A n/a B 72% |
1-(p-tolyl)ethylamine
A
(S)-1-(4-methylphenyl)ethylamine
B
(R)-4'-methyl-1-phenylethylamine
Conditions | Yield |
---|---|
With 6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl) hydrogen phthalate In isopropyl alcohol Heating; | A 65.7% B n/a |
Stage #1: 1-(p-tolyl)ethylamine With N-(1-(R)-phenylethyl)-malonamic acid In acetone Heating; Stage #2: With hydrogenchloride | A 55% B n/a |
Stage #1: 1-(p-tolyl)ethylamine With 5-(1,2-O-C(CH3)2-3,6-anhydro-α-D-glucofuranose)-H-phthalate In methanol for 0.05h; Heating; Stage #2: With hydrogenchloride |
isopropyl methoxyacetate
1-(p-tolyl)ethylamine
A
2-methoxy-N-[(1R)-1-(4-methylphenyl)ethyl]acetamide
B
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
With Novozym 435 at 23℃; for 3h; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; | A 45% B 45% |
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee; |
1-(p-tolyl)ethylamine
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
With D-(+)-camphoric acid | |
With N-Ac-Leu |
A
(S)-1-(4-methylphenyl)ethylamine
B
(R)-4'-methyl-1-phenylethylamine
Conditions | Yield |
---|---|
With platinum(IV) oxide; sodium periodate; hydrogen 1.) C6H6, 2.) CH3OH, RT, 5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
A
(S)-1-(4-methylphenyl)ethylamine
B
(R)-4'-methyl-1-phenylethylamine
Conditions | Yield |
---|---|
With platinum(IV) oxide; sodium periodate; hydrogen 1.) C6H6, 2.) CH3OH, RT, 5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
para-methylacetophenone
A
(S)-1-(4-methylphenyl)ethylamine
B
(R)-4'-methyl-1-phenylethylamine
Conditions | Yield |
---|---|
Stage #1: para-methylacetophenone With [((R)-tol-binap)RuCl2(DMF)x]; ammonia; ammonium formate In methanol at 85℃; for 21h; Leuckart-Wallach reaction; Stage #2: With hydrogenchloride In ethanol for 1h; Heating; Title compound not separated from byproducts; | |
Stage #1: para-methylacetophenone With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; reductive amination; Stage #2: racemate resolution; Further stages.; | |
Stage #1: para-methylacetophenone With 2-Hydroxybenzylamine; C24H34N2O2 In toluene at 110℃; for 72h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 24h; Overall yield = 52 %; | A n/a B n/a |
1-p-tolylethanone oxime
A
(S)-1-(4-methylphenyl)ethylamine
B
(R)-4'-methyl-1-phenylethylamine
Conditions | Yield |
---|---|
Stage #1: 1-p-tolylethanone oxime With diphenylsilane; silver trifluoromethanesulfonate In 1,2-dimethoxyethane at 20℃; for 40h; Stage #2: With hydrogenchloride In methanol; 1,2-dimethoxyethane Further stages. Title compound not separated from byproducts.; |
(E)-1-(4-methylphenyl)ethanone O-benzyl oxime
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; borane; enantiopure spiroborate ester In 1,4-dioxane for 36h; |
1-p-tolylethanone oxime
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 20 °C 2: borane; NaBH4 / enantiopure spiroborate ester / dioxane / 36 h View Scheme |
4-methylbenzaldehyde O-[(2R)-2-hydroxy-2-phenylethyl]oxime
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene; diethyl ether / 0.42 h / -20 °C 2: 72 percent / Mo(CO)6 / acetonitrile; H2O / 1 h / 85 °C View Scheme |
4-methyl-benzaldehyde
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 98 percent / TsOH / toluene / 0.5 h / Heating 2: toluene; diethyl ether / 0.42 h / -20 °C 3: 72 percent / Mo(CO)6 / acetonitrile; H2O / 1 h / 85 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 4 Angstroem molecular sieves / benzene / 24 h / Ambient temperature 2: 1.) H2, PtO2, 2.) NaIO4 / 1.) C6H6, 2.) CH3OH, RT, 5 h View Scheme | |
Multi-step reaction with 2 steps 1: 4 Angstroem molecular sieves / benzene / 24 h / Ambient temperature 2: 1.) H2, PtO2, 2.) NaIO4 / 1.) C6H6, 2.) CH3OH, RT, 5 h View Scheme |
4-methylacethophenone oxime
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanol; sodium 2: (1R)-cis-camphoric acid View Scheme |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; hydrogen; nickel In toluene at 70℃; under 75.0075 Torr; for 72h; Autoclave; Enzymatic reaction; optical yield given as %ee; |
para-methylacetophenone
B
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
With Chromobacterium violaceum ω-transaminase variant W60C at 37℃; for 12h; pH=7; Reagent/catalyst; pH-value; enantioselective reaction; | A n/a B n/a C n/a |
para-methylacetophenone
A
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: formamide / water / 10 h / 210 °C 1.2: 1 h / 100 °C / Reflux 2.1: Candida antarctica B lipase CAL-B acrylic resin / toluene / 72 h / 50 °C / Enzymatic reaction View Scheme |
1-(p-tolyl)ethylamine
ethyl acetate
A
(S)-1-(4-methylphenyl)ethylamine
Conditions | Yield |
---|---|
With Candida antarctica B lipase CAL-B acrylic resin In toluene at 50℃; for 72h; Enzymatic reaction; enantioselective reaction; | A n/a B 50 %Chromat. |
1-(p-tolyl)ethylamine
3-Methyl-2,4-pentanedione
A
(S)-1-(4-methylphenyl)ethylamine
D
(R)-4'-methyl-1-phenylethylamine
Conditions | Yield |
---|---|
With C74H89O4P In diethyl ether at -78 - -5℃; for 20h; Inert atmosphere; Molecular sieve; Resolution of racemate; | A n/a B n/a C n/a D n/a |
2-amino-5-methylhexane
3-Methyl-2,4-pentanedione
A
(S)-1-(4-methylphenyl)ethylamine
C
(R)-4'-methyl-1-phenylethylamine
Conditions | Yield |
---|---|
With C74H89O4P In diethyl ether at -78 - -5℃; for 20h; Inert atmosphere; Molecular sieve; Resolution of racemate; | A n/a B n/a C n/a |
1-(p-tolyl)ethylamine
A
(S)-1-(4-methylphenyl)ethylamine
B
para-methylacetophenone
Conditions | Yield |
---|---|
With (R)-amine dehydrogenase In dimethyl sulfoxide at 37℃; pH=8.5; Catalytic behavior; Resolution of racemate; Microbiological reaction; Enzymatic reaction; enantioselective reaction; |
4-methylethylbenzene
A
(S)-1-(4-methylphenyl)ethylamine
B
(R)-4'-methyl-1-phenylethylamine
C
4-ethylbenzylamine
Conditions | Yield |
---|---|
With C5H11NO*CHF3O3S In ethanol; water at 10℃; for 12h; pH=7.4; Inert atmosphere; Sealed tube; Enzymatic reaction; Overall yield = 48 percent; enantioselective reaction; | A n/a B n/a C n/a |
(S)-1-(4-methylphenyl)ethylamine
2-oxopropanal
Conditions | Yield |
---|---|
100% |
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