CAS No.181289-39-4,Hexanoic acid, 3-cyano-5-methyl-, ethyl ester, (3S)- Suppliers

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Basic Information

Molecular Structure:
CAS No.:	181289-39-4
Name:	Hexanoic acid, 3-cyano-5-methyl-, ethyl ester, (3S)-
Article Data:	9

Formula:	C10H17NO2
Molecular Weight:	183.25
Synonyms:	ethyl (S)-3-cyano-5-methylhexanoate;(S)-3-cyano-5-methyl hexanoic acid ethyl ester;(S)-ethyl 3-cyano-5-methylhexanoate;(S)-3-cyano-5-methyl-hexanoic acid ethyl ester;(S)-ethyl 3-cyano-5-methyl-hexanoate;
PSA:	50.09000
LogP:	2.12548

Synthetic route

: potassium cyanide

: 34993-63-0, 79918-80-2, 2351-89-5
5-methyl-2-hexenoic acid ethyl ester

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
With 1-(9-methylanthracene)-((R)-(6-hydroxy-4-quinolinyl)phenoxymethyl-2-yl)-5-ethenyl-1-azabicyclo[2.2.2]octane In hexane; water at 20℃; for 15h; Michael Addition; Green chemistry; stereoselective reaction;	93.4%

: 4-isobutyl-2-oxopyrrolidine-3-carboxylic acid

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid In water at 80 - 110℃;	80%

: 181289-17-8
(R,S)-3-cyano-5-methylhexanoic acid ethyl ester

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
With sodium hydroxide; Candida antarctica lipase B In water at 15℃; pH=7.2; Aqueous phosphate buffer; Resolution of racemate;	77%

: 1335223-63-6
(E)-ethyl 3-cyano-5-methylhex-2-enoate

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
With NADP In isopropyl alcohol at 30℃; for 96h; Enzymatic reaction; enantioselective reaction;	68.8%
With Citrobacter sp. N-ethylmaleimide reductase; NADPH; NADH In dimethyl sulfoxide at 30℃; for 22h; pH=7; Product distribution / selectivity; Enzymatic reaction; Aqueous phosphate buffer;	n/a
With nicotinamide-dependent cyclohexenone reductase from Zymomonas mobilis; NADH In aq. buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; stereoselective reaction;	n/a

: 350801-68-2
3-cyano-5-methyl-hex-3-enoic acid ethyl ester

A: 5-methyl-3-cyanohexanoic acid ethyl ester

B: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
With hydrogen; (Z,Z)-cycloocta-1,5-diene(R,R-1,2-bis(2,5-diethylphospholanyl)benzene)rhodium(I) tetrafluoroborate In methanol at 55℃; under 5171.48 Torr; Product distribution; Further Variations:; Reagents; Temperatures; Pressures;

: (3S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid

A: 181289-37-2
3-(S)-cyano-5-methyl-hexanoic acid

B: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
With water; sodium chloride In dimethyl sulfoxide at 88 - 135℃; for 20.5h;	A n/a B n/a

: (S)-2-ethoxycarbonyl-3-cyano-5-methylhexanoic acid sodium salt

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
With water; sodium chloride In toluene at 75 - 85℃; for 2h; Heating / reflux;

: 61-90-5
L-leucine

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium nitrite; sulfuric acid; potassium bromide / water / 6.5 h / -14 - 20 °C 2.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere 2.2: 25 °C / Inert atmosphere 3.1: phosphorus pentoxide / 80 °C / 12 Torr 4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C 5.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium nitrite; sulfuric acid; potassium bromide / water / 6.5 h / -14 - 20 °C 2.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere 2.2: 25 °C / Inert atmosphere 3.1: phosphorus pentoxide / 80 °C / 12 Torr 4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C 5.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C 6.1: sodium ethanolate / ethanol / 25 - 85 °C 7.1: sodium hydroxide / Candida antarctica lipase B / water / 15 °C / pH 7.2 / Aqueous phosphate buffer; Resolution of racemate View Scheme

Yield

Multi-step reaction with 5 steps
1.1: sodium nitrite; sulfuric acid; potassium bromide / water / 6.5 h / -14 - 20 °C
2.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere
2.2: 25 °C / Inert atmosphere
3.1: phosphorus pentoxide / 80 °C / 12 Torr
4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C
5.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C
View Scheme

Multi-step reaction with 7 steps
1.1: sodium nitrite; sulfuric acid; potassium bromide / water / 6.5 h / -14 - 20 °C
2.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere
2.2: 25 °C / Inert atmosphere
3.1: phosphorus pentoxide / 80 °C / 12 Torr
4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C
5.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C
6.1: sodium ethanolate / ethanol / 25 - 85 °C
7.1: sodium hydroxide / Candida antarctica lipase B / water / 15 °C / pH 7.2 / Aqueous phosphate buffer; Resolution of racemate
View Scheme

: 28659-87-2
(S)-2-bromo-4-methylpentanoic acid

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere 1.2: 25 °C / Inert atmosphere 2.1: phosphorus pentoxide / 80 °C / 12 Torr 3.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C 4.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C View Scheme
Multi-step reaction with 6 steps 1.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere 1.2: 25 °C / Inert atmosphere 2.1: phosphorus pentoxide / 80 °C / 12 Torr 3.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C 4.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C 5.1: sodium ethanolate / ethanol / 25 - 85 °C 6.1: sodium hydroxide / Candida antarctica lipase B / water / 15 °C / pH 7.2 / Aqueous phosphate buffer; Resolution of racemate View Scheme

Yield

Multi-step reaction with 4 steps
1.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere
1.2: 25 °C / Inert atmosphere
2.1: phosphorus pentoxide / 80 °C / 12 Torr
3.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C
4.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C
View Scheme

Multi-step reaction with 6 steps
1.1: thionyl chloride / cyclohexane / 13 h / 60 - 80 °C / Inert atmosphere
1.2: 25 °C / Inert atmosphere
2.1: phosphorus pentoxide / 80 °C / 12 Torr
3.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 25 °C
4.1: potassium chloride / water; dimethyl sulfoxide / 4 h / 150 - 160 °C
5.1: sodium ethanolate / ethanol / 25 - 85 °C
6.1: sodium hydroxide / Candida antarctica lipase B / water / 15 °C / pH 7.2 / Aqueous phosphate buffer; Resolution of racemate
View Scheme

: 7352-02-5
ethyl 2-cyano-4-methylpentanoate

: 181289-39-4
(S)-3-cyano-5-methylhexanoic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil (nujol) / 10 - 50 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide / 4 h / 150 - 160 °C 3.1: sodium hydroxide / Candida antarctica lipase B / water / 15 °C / pH 7.2 / Aqueous phosphate buffer; Resolution of racemate View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / 1,2-dimethoxyethane; paraffin oil (nujol) / 10 - 50 °C 1.2: 20 °C 2.1: dimethyl sulfoxide / 4 h / 150 - 160 °C 3.1: sodium hydroxide / Candida antarctica lipase B / water / 15 °C / pH 7.2 / Aqueous phosphate buffer; Resolution of racemate View Scheme