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181269-69-2

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181269-69-2 Usage

General Description

1-BOC-3-METHYL-PIPERIDIN-4-ONE is a chemical compound with the molecular formula C12H21NO3. It is a derivative of piperidin-4-one, which is a heterocyclic organic compound with a six-membered ring containing one nitrogen atom. The "1-BOC" in the name indicates the presence of a tert-butoxycarbonyl (BOC) protecting group at the 1-position of the piperidin-4-one ring. This protecting group is commonly used in organic synthesis to prevent unwanted reactions at specific sites in a molecule. 1-BOC-3-METHYL-PIPERIDIN-4-ONE is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. It is also a useful intermediate in the preparation of complex organic molecules.

Check Digit Verification of cas no

The CAS Registry Mumber 181269-69-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,1,2,6 and 9 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 181269-69:
(8*1)+(7*8)+(6*1)+(5*2)+(4*6)+(3*9)+(2*6)+(1*9)=152
152 % 10 = 2
So 181269-69-2 is a valid CAS Registry Number.
InChI:InChI=1/C11H19NO3/c1-8-7-12(6-5-9(8)13)10(14)15-11(2,3)4/h8H,5-7H2,1-4H3

181269-69-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylate

1.2 Other means of identification

Product number -
Other names 1-BOC-3-METHYL-PIPERIDIN-4-ONE

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:181269-69-2 SDS

181269-69-2Synthetic route

1-Benzyl-3-methyl-4-piperidon
34737-89-8

1-Benzyl-3-methyl-4-piperidon

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethyl acetate under 2068.65 Torr; for 24h;100%
With hydrogen; palladium 10% on activated carbon In ethanol at 20℃; under 2585.81 Torr; for 4h;97%
With hydrogen; palladium(II) hydroxide In methanol at 20℃; under 2844.39 Torr;95%
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

methyl iodide
74-88-4

methyl iodide

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; for 3h;
45%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 3h;
28%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With potassium hexamethylsilazane In tetrahydrofuran; toluene at 20℃; for 2h;
Stage #2: methyl iodide In tetrahydrofuran; toluene at 20℃;
22.5%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With sodium hydride In tetrahydrofuran; mineral oil at 20℃;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil
16%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 18h;
10%
3-methyl-4-piperidone
5773-58-0

3-methyl-4-piperidone

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

Conditions
ConditionsYield
With N,N-dimethylethylenediamine In dichloromethane at 20℃; for 2.5h;
With dmap; triethylamine In tetrahydrofuran; water at 20℃; for 18h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 1-Benzyl-3-methyl-4-piperidon With hydrogenchloride; hydrogen; palladium dihydroxide In 1,4-dioxane; methanol under 2585.81 Torr;
Stage #2: di-tert-butyl dicarbonate With triethylamine In tetrahydrofuran for 2h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

C14H23NO5
1159982-52-1

C14H23NO5

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: C14H23NO5 With hydrogenchloride In water for 48h; Reflux;
Stage #2: di-tert-butyl dicarbonate With sodium carbonate In tetrahydrofuran; water
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

tert-Butyl 4-hydroxy-3-methylpiperidine-1-carboxylate
181269-70-5

tert-Butyl 4-hydroxy-3-methylpiperidine-1-carboxylate

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 3.5h;100%
With methanol; sodium tetrahydroborate at 0 - 25℃; for 3.5h;100%
With sodium tetrahydroborate In ethanol at 0℃; for 0.5h;88%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

3-methyl-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
1240971-20-3

3-methyl-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.5h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 25℃; for 2.5h;
97%
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.5h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; for 16h;
78%
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 1h;
61%
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 25℃; for 3h;
198 mg
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 1h; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -70 - 0℃; for 4h;
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

(S)-2-(2-(methylsulfonyl)ethyl)pyrrolidine hydrochloride

(S)-2-(2-(methylsulfonyl)ethyl)pyrrolidine hydrochloride

C13H26N2O2S*ClH

C13H26N2O2S*ClH

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; (S)-2-(2-(methylsulfonyl)ethyl)pyrrolidine hydrochloride With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 6h;
Stage #2: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 4h;
96%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

diethyl {3-[(5-chloropyridin-2-yl)oxy]benzyl}phosphonate
1191250-62-0

diethyl {3-[(5-chloropyridin-2-yl)oxy]benzyl}phosphonate

5-chloro-2-{3-[(3-methylpiperidin-4-ylidene)methyl]phenoxy}pyridine

5-chloro-2-{3-[(3-methylpiperidin-4-ylidene)methyl]phenoxy}pyridine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h;90%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h;
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

2-(5-methoxy-2-nitrophenyl)-ethylamine
180149-25-1

2-(5-methoxy-2-nitrophenyl)-ethylamine

tert-butyl 4-[2-(5-methoxy-2-nitro-phenyl)-ethylamino]-3-methyl-piperidine-1-carboxylate
1146733-30-3

tert-butyl 4-[2-(5-methoxy-2-nitro-phenyl)-ethylamino]-3-methyl-piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 3h;90%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

tert-butyl 4-methyl-1-oxa-6-azaspiro[2.5]octane-6-carboxylate

tert-butyl 4-methyl-1-oxa-6-azaspiro[2.5]octane-6-carboxylate

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane; dimethyl sulfoxide at 0 - 5℃; for 1h;90%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

tert-butyl 4-hydroxy-3-methyl-4-phenylpiperidine-1-carboxylate

tert-butyl 4-hydroxy-3-methyl-4-phenylpiperidine-1-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 24h;84%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

tert-butyl 3-methyl-4-methylidenepiperidine-1-carboxylate
336182-47-9

tert-butyl 3-methyl-4-methylidenepiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃;
Stage #2: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate In tetrahydrofuran at 20℃; for 1h;
83%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;
60%
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 16h;
bromochlorobenzene
106-39-8

bromochlorobenzene

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

4-(4-chloro-phenyl)-4-hydroxy-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

4-(4-chloro-phenyl)-4-hydroxy-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: bromochlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate In tetrahydrofuran; hexane at -78 - -20℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water
83%
Stage #1: bromochlorobenzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.75h;
Stage #2: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate In tetrahydrofuran; hexanes at -78℃; for 2h;
79%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

sodium methylate
124-41-4

sodium methylate

4-methoxycarbonylmethylene-3-methylpiperidine-1-carboxylic acid t-butyl ester
502609-65-6

4-methoxycarbonylmethylene-3-methylpiperidine-1-carboxylic acid t-butyl ester

Conditions
ConditionsYield
In tetrahydrofuran; methanol at 20℃; for 4h;82.5%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

tert-butyl 4-amino-3-methylpiperidine-1-carboxylate
900642-17-3

tert-butyl 4-amino-3-methylpiperidine-1-carboxylate

Conditions
ConditionsYield
With ammonium formate; sodium cyanoborohydride In methanol at 30℃; for 16h; Temperature; Molecular sieve;80%
With ammonium formate; sodium cyanoborohydride In methanol at 20℃; for 3h; Molecular sieve;60%
With formic acid; ammonium formate; sodium cyanoborohydride In methanol at 20℃; for 2h;
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

2-[3-(diethoxyphosphorylmethyl)phenoxy]-5-(trifluoromethyl)pyridine
1020325-38-5

2-[3-(diethoxyphosphorylmethyl)phenoxy]-5-(trifluoromethyl)pyridine

2-{3-[(3-methylpiperidin-4-ylidene)methyl]phenoxy}-5-(trifluoromethyl)pyridine
1191288-06-8

2-{3-[(3-methylpiperidin-4-ylidene)methyl]phenoxy}-5-(trifluoromethyl)pyridine

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; 2-[3-(diethoxyphosphorylmethyl)phenoxy]-5-(trifluoromethyl)pyridine With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
79%
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; 2-[3-(diethoxyphosphorylmethyl)phenoxy]-5-(trifluoromethyl)pyridine With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
79%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

3-methyl-4-piperidone
5773-58-0

3-methyl-4-piperidone

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
Stage #2: With water In dichloromethane; water
75%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

1,1-dimethylethyl 4-methyl-1-oxa-6-azaspiro[2.5]octane-6-carboxylate
862669-17-8

1,1-dimethylethyl 4-methyl-1-oxa-6-azaspiro[2.5]octane-6-carboxylate

Conditions
ConditionsYield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 0 - 20℃; for 2h;
Stage #2: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate In dimethyl sulfoxide; mineral oil at 0 - 20℃; for 2h;
75%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

methyl (S)-3-(pyrrolidin-2-yl)propanoate
689303-75-1

methyl (S)-3-(pyrrolidin-2-yl)propanoate

tert-butyl 4-((S)-2-(3-methoxy-3-oxopropyl)pyrrolidin-1-yl)-3-methylpiperidine-1-carboxylate

tert-butyl 4-((S)-2-(3-methoxy-3-oxopropyl)pyrrolidin-1-yl)-3-methylpiperidine-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 16h;75%
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; methyl (S)-3-(pyrrolidin-2-yl)propanoate In 1,2-dichloro-ethane at 20℃; for 0.5h;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃;
37%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

Diethyl 3-(5-bromopyridin-2-yloxy)benzylphosphonate
1020326-79-7

Diethyl 3-(5-bromopyridin-2-yloxy)benzylphosphonate

5-bromo-2-{3-[(3-methylpiperidin-4-ylidene)methyl]phenoxy}pyridine
1191250-55-1

5-bromo-2-{3-[(3-methylpiperidin-4-ylidene)methyl]phenoxy}pyridine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h;72%
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; Diethyl 3-(5-bromopyridin-2-yloxy)benzylphosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
72%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

benzyltriphenylphosphonium bromide
1449-46-3

benzyltriphenylphosphonium bromide

tert-butyl 4-benzylidene-3-methylpiperidine-1-carboxylate

tert-butyl 4-benzylidene-3-methylpiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: benzyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;
Stage #2: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate In tetrahydrofuran at 20℃; for 3h;
63%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

2-propynamide
7341-96-0

2-propynamide

tert-butyl 8-methyl-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate
1401034-50-1

tert-butyl 8-methyl-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With pyrrolidine In toluene for 5h; Reflux;
Stage #2: 2-propynamide In toluene Reflux;
55%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

p-tolylsulfonylmethyl isocyanide
5697-44-9

p-tolylsulfonylmethyl isocyanide

tert-butyl 4-cyano-3-methylpiperidine-1-carboxylate

tert-butyl 4-cyano-3-methylpiperidine-1-carboxylate

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane at 0 - 25℃; for 16h; Inert atmosphere;50.4%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide
145100-51-2

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

3-methyl-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
1240971-20-3

3-methyl-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With potassium hexamethylsilazane In tetrahydrofuran at -78 - 20℃; for 3.5h;
Stage #2: N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide In tetrahydrofuran at -78 - 20℃;
47%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

tert-butyl 3-(2-ethoxy-2-oxoacetyl)-5-methyl-4-oxopiperidine-1-carboxylate

tert-butyl 3-(2-ethoxy-2-oxoacetyl)-5-methyl-4-oxopiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: oxalic acid diethyl ester In tetrahydrofuran at 20℃; for 2h;
45.6%
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -60℃; for 0.5h;
Stage #2: oxalic acid diethyl ester at -60 - 20℃; for 1h;
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

2-iodo-1-(2,2,2-trifluoroethyl)-1H-indol-4-amine

2-iodo-1-(2,2,2-trifluoroethyl)-1H-indol-4-amine

tert-butyl 4-((2-iodo-1-(2,2,2-trifluoroethyl)-1H-indol-4-yl)amino)-3-methylpiperidine-1-carboxylate

tert-butyl 4-((2-iodo-1-(2,2,2-trifluoroethyl)-1H-indol-4-yl)amino)-3-methylpiperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; 2-iodo-1-(2,2,2-trifluoroethyl)-1H-indol-4-amine With chloro-trimethyl-silane In N,N-dimethyl-formamide at 0℃; for 2h;
Stage #2: With borane-THF In N,N-dimethyl-formamide at 0 - 25℃; for 1h; Temperature; Reagent/catalyst; Inert atmosphere;
45.28%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

(S)-1-Pyrrolidin-2-yl-methanol
23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

tert-butyl 4-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3-methylpiperidine-1-carboxylate

tert-butyl 4-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3-methylpiperidine-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 16h;40%
2-cyanomethylbenzothiazole
56278-50-3

2-cyanomethylbenzothiazole

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

tert-butyl 2-amino-3-(benzo[d]thiazol-2-yl)-4-methyl-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate

tert-butyl 2-amino-3-(benzo[d]thiazol-2-yl)-4-methyl-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate

Conditions
ConditionsYield
With morpholine; sulfur at 85℃; for 12h;39%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

2-methyl-2-thiopseudouronium sulfate

2-methyl-2-thiopseudouronium sulfate

tert-butyl 8-methyl-2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate
1567965-66-5

tert-butyl 8-methyl-2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; N,N-dimethyl-formamide dimethyl acetal at 80℃; for 12h;
Stage #2: 2-methyl-2-thiopseudouronium sulfate With sodium ethanolate In ethanol at 80℃; for 12.5h;
36%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

CYANAMID
420-04-2

CYANAMID

C12H19N3O2S
1253415-55-2

C12H19N3O2S

Conditions
ConditionsYield
With pyridine; sulfur at 100℃; for 3h;31.3%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

(S)-2-(pyrrolidin-2-yl)ethane-1-sulfonamide

(S)-2-(pyrrolidin-2-yl)ethane-1-sulfonamide

2-((S)-1-((3R,4S)-3-methylpiperidin-4-yl)pyrrolidin-2-yl)ethane-1-sulfonamide

2-((S)-1-((3R,4S)-3-methylpiperidin-4-yl)pyrrolidin-2-yl)ethane-1-sulfonamide

Conditions
ConditionsYield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate; (S)-2-(pyrrolidin-2-yl)ethane-1-sulfonamide With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 16h;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
22%
tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate
181269-69-2

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

(3R,4R)-3-methyl-4-(1-(S)-phenyl-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester
723308-56-3

(3R,4R)-3-methyl-4-(1-(S)-phenyl-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With sodium triacetoxyborohydride In dichloromethane at 20℃;10%
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;10%

181269-69-2Relevant articles and documents

Selective α-Methylation of Ketones

Frolov, Andriy I.,Ostapchuk, Eugeniy N.,Pashenko, Alexander E.,Chuchvera, Yaroslav O.,Rusanov, Eduard B.,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.

, p. 7333 - 7346 (2021/06/28)

The convenient and scalable preparative approach for the two-step α-methylation of ketones is described. The optimized protocols for regioselective preparation of enaminones with further diastereoselective and functional groups tolerant hydrogenation to α-methylketones are developed. The scope and limitations of the proposed methodology are discussed. The advantages compared to known procedures are demonstrated. The unexpected role of acetone in the hydrogenation is suggested. The evaluation of the method for both early building block synthesis and late-stage CH-functionalization is shown. The elaborate procedures' preparability and scalability are demonstrated by the synthesis of several α-methyl ketones up to 100 g amount.

INHIBITORS OF MUTANT ISOCITRATE DEHYDROGENASES AND COMPOSITIONS AND METHODS THEREOF

-

Paragraph 00128, (2018/04/27)

The invention provides novel chemical compounds useful for treating cancer, or a related disease or disorder thereof, and pharmaceutical composition and methods of preparation and use thereof.

NRF2 ACTIVATOR

-

Page/Page column 98-99, (2018/07/29)

Provided are compounds of Formula I, or pharmaceutically acceptable salts thereof, and methods for their use and production.

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