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74572-04-6

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74572-04-6 Usage

Chemical Properties

colourless liquid

Uses

(R)-3-Methylmorpholine is useful for the discovery of (2S)-8-[(3R)-3-Methylmorpholin-4-yl]-1-(3-methyl-2-oxobutyl)-2-(trifluoromethyl)-3,4-dihydro-2H-pyrimido[1,2-a]pyrimidin-6-one, an inhibitor of Vps34 for the treatment of solid tumors.

Check Digit Verification of cas no

The CAS Registry Mumber 74572-04-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,4,5,7 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 74572-04:
(7*7)+(6*4)+(5*5)+(4*7)+(3*2)+(2*0)+(1*4)=136
136 % 10 = 6
So 74572-04-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO/c1-5-4-7-3-2-6-5/h5-6H,2-4H2,1H3/t5-/m1/s1

74572-04-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-3-Methylmorpholine

1.2 Other means of identification

Product number -
Other names (3R)-3-methylmorpholine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:74572-04-6 SDS

74572-04-6Synthetic route

(R)-4-(4-methoxybenzyl)-3-methylmorpholine
954133-47-2

(R)-4-(4-methoxybenzyl)-3-methylmorpholine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 50℃; under 9500.64 Torr; for 18h;83%
(5R)-5-methylmorpholin-3-one
119844-67-6

(5R)-5-methylmorpholin-3-one

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h;75%
Stage #1: (5R)-5-methylmorpholin-3-one With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 15.5h; Heating / reflux;
Stage #2: With hydrogenchloride; ethanol In tetrahydrofuran
(R)-2-(2-hydroxyethylamino)propan-1-ol

(R)-2-(2-hydroxyethylamino)propan-1-ol

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
Stage #1: (R)-2-(2-hydroxyethylamino)propan-1-ol With sulfuric acid at 140℃; for 14h;
Stage #2: With sodium hydroxide In water at 0℃;
65%
2-(prop-2-yn-1-yloxy)ethan-1-amine
122116-12-5

2-(prop-2-yn-1-yloxy)ethan-1-amine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
Stage #1: 2-(prop-2-yn-1-yloxy)ethan-1-amine With C42H58N4O2Ti In toluene at 110℃; for 14h; Inert atmosphere; Schlenk technique;
Stage #2: With formic acid; [{(1S,2S-N-p-toluenesulfonyl-1,2-diphenylethanediamine)}(η6-p-cymene)RuCl]; triethylamine In N,N-dimethyl-formamide; toluene at 20℃; for 14h; Inert atmosphere; Schlenk technique; enantioselective reaction;
65%
Multi-step reaction with 2 steps
1: bis(N-2,6-diisoprpylphenylbenzamidato)bis(dimethylamido)titanium (IV) / toluene / 14 h / 110 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube
2: formic acid; [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); triethylamine / N,N-dimethyl-formamide / 23 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1: bis(N-2,6-diisoprpylphenylbenzamidato)bis(dimethylamido)titanium (IV) / toluene / 14 h / 110 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube
2: formic acid; silver trifluoromethanesulfonate; [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); triethylamine / N,N-dimethyl-formamide / 16 h / 23 °C / Inert atmosphere; Schlenk technique
View Scheme
(3R)-3-methyl-4-(phenylmethyl)morpholine
74571-98-5

(3R)-3-methyl-4-(phenylmethyl)morpholine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal at 80℃; under 45600 - 60800 Torr; for 2h;
With hydrogen; palladium 10% on activated carbon In ethanol under 2585.81 Torr;
With hydrogen; hydrogenchloride; palladium 10% on activated carbon In 1,4-dioxane; ethyl acetate under 2068.65 Torr; for 18h;
(R)-2-[Benzyl-(2-hydroxy-ethyl)-amino]-propan-1-ol
74571-95-2

(R)-2-[Benzyl-(2-hydroxy-ethyl)-amino]-propan-1-ol

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70percent H2SO4 / 15 h / 140 °C
2: H2 / 10percent Pd/C / 2 h / 80 °C / 45600 - 60800 Torr
View Scheme
(R)-2-bromo-N-(1-hydroxypropan-2-yl)-N-(4-methoxybenzyl)acetamide
1445590-35-1

(R)-2-bromo-N-(1-hydroxypropan-2-yl)-N-(4-methoxybenzyl)acetamide

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / tetrahydrofuran / 25 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Reflux
3: palladium on activated charcoal; hydrogen / methanol / 18 h / 50 °C / 9500.64 Torr
View Scheme
(R)-4-(4-methoxybenzyl)-5-methylmorpholin-3-one
570398-22-0

(R)-4-(4-methoxybenzyl)-5-methylmorpholin-3-one

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Reflux
2: palladium on activated charcoal; hydrogen / methanol / 18 h / 50 °C / 9500.64 Torr
View Scheme
3-methylmorpholine
42185-06-8

3-methylmorpholine

C14H15NO4

C14H15NO4

A

C8H15NO2

C8H15NO2

B

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
In dichloromethane at 23℃; Inert atmosphere;
2-chloro-N-(2-hydroxy-1-methyl-ethyl)-acetamide
1057322-63-0

2-chloro-N-(2-hydroxy-1-methyl-ethyl)-acetamide

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium tert-butylate / dichloromethane; isopropyl alcohol / 1 h / 0 - 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C
View Scheme
C5H9NO

C5H9NO

A

(S)-3-methylmorpholine
350595-57-2

(S)-3-methylmorpholine

B

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
With [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); formic acid; silver trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 23℃; for 16h; Inert atmosphere; Schlenk technique; enantioselective reaction;A n/a
B n/a
C5H9NO

C5H9NO

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
With [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); formic acid; triethylamine In N,N-dimethyl-formamide at 23℃; Reagent/catalyst; Inert atmosphere; Schlenk technique; enantioselective reaction;n/a
N-(tert-butyloxycarbonyl)-2-(propargyloxy)aminoethane
634926-63-9

N-(tert-butyloxycarbonyl)-2-(propargyloxy)aminoethane

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol / 0 - 23 °C
2: bis(N-2,6-diisoprpylphenylbenzamidato)bis(dimethylamido)titanium (IV) / toluene / 14 h / 110 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube
3: formic acid; [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); triethylamine / N,N-dimethyl-formamide / 23 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 3 steps
1: methanol / 0 - 23 °C
2: bis(N-2,6-diisoprpylphenylbenzamidato)bis(dimethylamido)titanium (IV) / toluene / 14 h / 110 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube
3: formic acid; silver trifluoromethanesulfonate; [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); triethylamine / N,N-dimethyl-formamide / 16 h / 23 °C / Inert atmosphere; Schlenk technique
View Scheme
4,6-Dichloro-2-(methylthio)pyrimidine
6299-25-8

4,6-Dichloro-2-(methylthio)pyrimidine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(3R)-4-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-3-methylmorpholine

(3R)-4-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-3-methylmorpholine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 16h;99%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃;68.1%
3,6-di-bromo-isothiazolo[4,3-b]pyridine

3,6-di-bromo-isothiazolo[4,3-b]pyridine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-4-(6-bromoisothiazolo[4,3-b]pyridin-3-yl)-3-methylmorpholine

(R)-4-(6-bromoisothiazolo[4,3-b]pyridin-3-yl)-3-methylmorpholine

Conditions
ConditionsYield
In ethanol Reflux;97%
2-chloro-N-methyl-N-(6-(2-morphplino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl)acetamide
1257236-41-1

2-chloro-N-methyl-N-(6-(2-morphplino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl)acetamide

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

N-methyl-2-[(3R)-3-methylmorpholin-4-yl]-N-[6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl]acetamide
1257234-75-5

N-methyl-2-[(3R)-3-methylmorpholin-4-yl]-N-[6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl]acetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane; ISOPROPYLAMIDE at 60℃; for 2h;95%
(1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentanecarboxylic acid
1445591-92-3

(1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentanecarboxylic acid

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

((1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentyl)((R)-3-methylmorpholino)methanone
1445590-41-9

((1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentyl)((R)-3-methylmorpholino)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0 - 20℃; for 2h;95%
(1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-methoxycyclopentanecarboxylic acid
1445592-12-0

(1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-methoxycyclopentanecarboxylic acid

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

((1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-methoxycyclopentyl)((R)-3-methylmorpholino)methanone
1445590-87-3

((1R,2R)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-methoxycyclopentyl)((R)-3-methylmorpholino)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h;95%
(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

acetyl chloride
75-36-5

acetyl chloride

1-[(3R)-3-methylmorpholin-4-yl]ethan-1-one
1257237-31-2

1-[(3R)-3-methylmorpholin-4-yl]ethan-1-one

Conditions
ConditionsYield
Stage #1: (3R)-3-methylmorpholine With potassium carbonate In dichloromethane at 20℃; for 0.5h;
Stage #2: acetyl chloride In dichloromethane at 20℃; for 18h;
95%
Stage #1: (3R)-3-methylmorpholine With potassium carbonate In dichloromethane at 0℃; for 0.5h;
Stage #2: acetyl chloride In dichloromethane at 25℃; for 16h;
88%
Stage #1: (3R)-3-methylmorpholine With potassium carbonate In dichloromethane at 20℃; for 0.5h;
Stage #2: acetyl chloride In dichloromethane at 20℃; for 18h;
2,4-dichloro-6-piperidin-1-yl-[1,3,5]triazine
19371-31-4

2,4-dichloro-6-piperidin-1-yl-[1,3,5]triazine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

2-chloro-4-[(3R)-3-methylmorpholin-4-yl]-6-(piperidin-1-yl)-1,3,5-triazine

2-chloro-4-[(3R)-3-methylmorpholin-4-yl]-6-(piperidin-1-yl)-1,3,5-triazine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; dichloromethane at 20℃;95%
(8S)-2-chloro-3-fluoro-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one
1260585-63-4

(8S)-2-chloro-3-fluoro-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(2S)-7-fluoro-8-[(3R)-3-methylmorpholin-4-yl]-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one
1523412-61-4

(2S)-7-fluoro-8-[(3R)-3-methylmorpholin-4-yl]-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Conditions
ConditionsYield
at 100℃; for 18h;91%
2,6-Dichloro-4-morpholino-1,3,5-triazine
6601-22-5

2,6-Dichloro-4-morpholino-1,3,5-triazine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

2-chloro-4-[(3R)-3-methylmorpholin-4-yl]-6-(morpholin-4-yl)-1,3,5-triazine

2-chloro-4-[(3R)-3-methylmorpholin-4-yl]-6-(morpholin-4-yl)-1,3,5-triazine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 0 - 20℃; Suzuki Coupling;91%
With N-ethyl-N,N-diisopropylamine In ethanol at 0 - 20℃;91%
With N-ethyl-N,N-diisopropylamine In ethanol at 0 - 20℃;
With N-ethyl-N,N-diisopropylamine
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(3R,3′R)-4,4′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(3-methylmorpholine)

(3R,3′R)-4,4′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(3-methylmorpholine)

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;91%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;91%
In dichloromethane at 0 - 20℃;
(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

2,4-dichloro-6-(4-nitrophenyl)-1,3,5-triazine
90415-38-6

2,4-dichloro-6-(4-nitrophenyl)-1,3,5-triazine

(R)-4-(4-chloro-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-methylmorpholine

(R)-4-(4-chloro-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-methylmorpholine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone at 0 - 20℃; for 20h;90%
3-(2,6-difluoropyridin-4-yl)-4-methylaniline

3-(2,6-difluoropyridin-4-yl)-4-methylaniline

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-3-(2-fluoro-6-(3-methylmorpholino)pyridin-4-yl)-4-methylaniline

(R)-3-(2-fluoro-6-(3-methylmorpholino)pyridin-4-yl)-4-methylaniline

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 18h;90%
(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

6-bromo-4-chlorothieno[2,3-d]pyrimidine
56844-12-3

6-bromo-4-chlorothieno[2,3-d]pyrimidine

(R)-4-(6-bromothieno[2,3-d]pyrimidin-4-yl)-3-methylmorpholine

(R)-4-(6-bromothieno[2,3-d]pyrimidin-4-yl)-3-methylmorpholine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 100℃;88%
2,6-dichloropyrimidine-4-carbonitrile

2,6-dichloropyrimidine-4-carbonitrile

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidine-4-carbonitrile

2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidine-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1.5h;87.47%
(3R,5S)-4-(4,6-dichloro-1,3,5-triazin-2-yl)-3,5-dimethylmorpholine

(3R,5S)-4-(4,6-dichloro-1,3,5-triazin-2-yl)-3,5-dimethylmorpholine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(3R,5S)-4-(4-chloro-6-((R)-3-methylmorpholino)-1,3,5-triazin-2-yl)-3,5-dimethylmorpholine

(3R,5S)-4-(4-chloro-6-((R)-3-methylmorpholino)-1,3,5-triazin-2-yl)-3,5-dimethylmorpholine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;87%
2,6-dichloro-4-pyrimidinecarboxylic acid
16492-28-7

2,6-dichloro-4-pyrimidinecarboxylic acid

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

methyl 2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate
1233339-69-9

methyl 2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h;86%
(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

2,6-dichloropyrimidine-4-carboxylic acid methyl ester
6299-85-0

2,6-dichloropyrimidine-4-carboxylic acid methyl ester

methyl 2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate
1233339-69-9

methyl 2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h;86%
With triethylamine In dichloromethane at 20℃; for 18h;79.19%
With triethylamine In dichloromethane at 20℃; for 16h; Temperature;70%
With triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;9%
2,6-dichloro-3-nitropyridin-4-amine
2897-43-0

2,6-dichloro-3-nitropyridin-4-amine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-6-chloro-2-(3-methylmorpholino)-3-nitropyridin-4-amine

(R)-6-chloro-2-(3-methylmorpholino)-3-nitropyridin-4-amine

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl acetamide at 80℃; for 3h;86%
bromobenzene
108-86-1

bromobenzene

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-3-methyl-4-phenylmorpholine

(R)-3-methyl-4-phenylmorpholine

Conditions
ConditionsYield
With bis(tri-tert-butylphasphine)palladium dichloride; potassium tert-butylate In toluene for 3h; Reflux;84%
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 90℃; for 24h;5%
(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-3-methyl-4-tosylmorpholine
1438397-95-5

(R)-3-methyl-4-tosylmorpholine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;83%
With triethylamine In dichloromethane at 0 - 23℃;
(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

piperic acid
136-72-1

piperic acid

(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-((R)-3-methylmorpholino)penta-2,4-dien-1-one

(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-((R)-3-methylmorpholino)penta-2,4-dien-1-one

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 8h;83%
(1S,2S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentanecarboxylic acid hydrochloride

(1S,2S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentanecarboxylic acid hydrochloride

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

((1S,2S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentyl)((R)-3-methylmorpholino)methanone
1445590-70-4

((1S,2S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)cyclopentyl)((R)-3-methylmorpholino)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h;82%
2,4,6-trichloropyrimidine
3764-01-0

2,4,6-trichloropyrimidine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(3R)-4-(2,6-dichloropyrimidin-4-yl)-3-methylmorpholine

(3R)-4-(2,6-dichloropyrimidin-4-yl)-3-methylmorpholine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 65℃; for 12h; Cooling with ice;81.2%
With triethylamine In ethanol at 20℃; for 16h;71%
With triethylamine In ethanol at 20℃; for 16h;71%
2,4-dichloro-6-((methylsulfonyl)methyl)pyrimidine

2,4-dichloro-6-((methylsulfonyl)methyl)pyrimidine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-4-(2-chloro-6-(methylsulfonylmethyl)pyrimidin-4-yl)-3-methylmorpholine
1233339-73-5

(R)-4-(2-chloro-6-(methylsulfonylmethyl)pyrimidin-4-yl)-3-methylmorpholine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;81%
5,7-dichloro-[1,3]thiazolo[5,4-d]pyrimidine
13479-88-4

5,7-dichloro-[1,3]thiazolo[5,4-d]pyrimidine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-4-(5-chlorothiazolo[5,4-d]pyrimidin-7-yl)-3-methylmorpholine

(R)-4-(5-chlorothiazolo[5,4-d]pyrimidin-7-yl)-3-methylmorpholine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 1.5h; Inert atmosphere;80%
ethyl 2-(4-formylphenyl)thiazole-4-carboxylate

ethyl 2-(4-formylphenyl)thiazole-4-carboxylate

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-2-(4-((3-methylmorpholine)methyl)phenyl)thiazole-4-carboxylic acid ethyl ester

(R)-2-(4-((3-methylmorpholine)methyl)phenyl)thiazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl 2-(4-formylphenyl)thiazole-4-carboxylate; (3R)-3-methylmorpholine In dichloromethane at 20 - 30℃; for 0.5h; Inert atmosphere;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 30℃; for 16h; Cooling with ice;
77.3%
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

2,4-dichloro-6-[(3R)-3-methylmorpholin-4-yl]-1,3,5-triazine

2,4-dichloro-6-[(3R)-3-methylmorpholin-4-yl]-1,3,5-triazine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -50℃; for 2h;76%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -50℃; for 2h;76%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -50℃; for 10h;
4,6-dichloro-5-nitropyrimidine
4316-93-2

4,6-dichloro-5-nitropyrimidine

(3R)-3-methylmorpholine
74572-04-6

(3R)-3-methylmorpholine

(R)-4-(6-chloro-5-nitropyrimidin-4-yl)-3-methylmorpholine

(R)-4-(6-chloro-5-nitropyrimidin-4-yl)-3-methylmorpholine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0℃; for 0.5h;75%

74572-04-6Downstream Products

74572-04-6Relevant articles and documents

Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (: R)-2-phenoxypropanoate

Bartashevich, Ekaterina V.,Chulakov, Evgeny N.,Ezhikova, Marina A.,Gruzdev, Dmitry A.,Kodess, Mikhail I.,Korolyova, Marina A.,Krasnov, Victor P.,Levit, Galina L.,Tumashov, Andrey A.,Vakarov, Sergey A.

supporting information, p. 862 - 869 (2022/02/03)

The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at -40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.

A concise and efficient synthesis of substituted morpholines

Dugar, Sundeep,Sharma, Amit,Kuila, Bilash,Mahajan, Dinesh,Dwivedi, Sandeep,Tripathi, Vinayak

, (2015/02/19)

A simple and efficient method has been developed for the synthesis of substituted morpholines by a sequence of coupling, cyclization, and reduction reactions of easily available amino alcohols and α-halo acid chlorides. Various mono-, di-, and trisubstituted morpholines, spiro morpholines, and ring-fused morpholines, as well as morpholine homologues, were synthesized in good to excellent yields by a single methodology under similar reaction conditions. The method was also used in a multigram synthesis of (3S)-3-methylmorpholine.

NOVEL HEPATITIS C VIRUS INHIBITORS

-

Page/Page column 39; 40, (2013/07/05)

The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

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