(1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid

Base Information

Chemical Name:(1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid
CAS No.:1443769-14-9
Molecular Formula:C₁₆H₁₉NO₄
Molecular Weight:289.331
Hs Code.:

Synonyms:(1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid

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Chemical Property of (1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid

Chemical Property:

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Technology Process of (1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid

There total 7 articles about (1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

: 1443768-78-2
(4aS,8aS)-N-benzyloxycarbonyl-2,4,4a,5,8,8a-hexahydro-1H-benzo[d][1,3]oxazinan-4-one

: 1443769-14-9
(1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1016/j.tet.2013.05.016

Reference yield:

: 78553-51-2
(S)-2-(benzyloxycarbonylamino)pent-4-enoic acid

: 1443769-14-9
(1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 4-methyl-morpholine / tetrahydrofuran / 0.25 h / -15 °C

2.1: tetrahydrofuran; dichloromethane / -15 - 25 °C

3.1: silver trifluoroacetate / water; 1,4-dioxane / Sonication

4.1: camphor-10-sulfonic acid / toluene / 90 °C / Molecular sieve; Inert atmosphere

5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.67 h / -78 °C / Inert atmosphere

5.2: -78 - -40 °C / Inert atmosphere

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / Reflux; Inert atmosphere

7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane

With 4-methyl-morpholine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; silver trifluoroacetate; potassium hexamethylsilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2013.05.016

Reference yield:

: C₁₆H₁₉NO₆

: 1443769-14-9
(1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran; dichloromethane / -15 - 25 °C

2.1: silver trifluoroacetate / water; 1,4-dioxane / Sonication

3.1: camphor-10-sulfonic acid / toluene / 90 °C / Molecular sieve; Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.67 h / -78 °C / Inert atmosphere

4.2: -78 - -40 °C / Inert atmosphere

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / Reflux; Inert atmosphere

6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; silver trifluoroacetate; potassium hexamethylsilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2013.05.016