((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester

Base Information

• Chemical Name: ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester
• CAS No.: 750594-83-3
• Molecular Formula: C₁₀H₁₉NO₃
• Molecular Weight: 201.266
• Mol file: 750594-83-3.mol

Synonyms:((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester

Chemical Property of ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester

There total 10 articles about ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester 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: 81.0%

{(S)-1-Cyclohexyl-2-[(2S,5R)-2-isopropyl-5-methyl-cyclohex-(E)-ylidene]-ethyl}-carbamic acid methyl ester (750594-74-2) → ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester (750594-83-3)

Guidance literature:

{(S)-1-Cyclohexyl-2-[(2S,5R)-2-isopropyl-5-methyl-cyclohex-(E)-ylidene]-ethyl}-carbamic acid methyl ester; With oil scarlet; ozone; In dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 15h;

DOI:10.1021/ol048936q

Reference yield:

1,1-dibromo-2-cyclohexylethene (60754-49-6) → ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester (750594-83-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

1.2: 5.56 g / tetrahydrofuran; hexane / 18 h / -78 - 20 °C

2.1: 91 percent / Red-Al / tetrahydrofuran; toluene / 15 h / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

3.2: tetrahydrofuran; hexane / 2 h / 0 - 20 °C

4.1: t-BuOK; s-BuLi / cyclohexane / 2.5 h / -78 - -50 °C

4.2: CuCN / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

4.3: 80 percent / tetrahydrofuran; cyclohexane / 4 h / -78 - 20 °C

5.1: 100 percent / FeCl₃ / diethyl ether / 15 h / 20 °C

6.1: 96 percent / K₂CO₃ / methanol / 16 h / 20 °C

7.1: 89 percent / Jones reagent / acetone / 1 h / 20 °C

8.1: DPPA; Et₃N / toluene / 1 h / Heating

8.2: 69 percent / methanol / 1 h / Heating

9.1: O₃; sudan III / CH₂Cl₂ / -78 °C

9.2: 81 percent / NaBH₄ / methanol / 15 h / 20 °C

With n-butyllithium; jones reagent; oil scarlet; diphenyl-phosphinic acid; potassium tert-butylate; sec.-butyllithium; iron(III) chloride; potassium carbonate; ozone; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; acetone; toluene; 8.1: Curtius rearrangement;

DOI:10.1021/ol048936q

Reference yield:

cyclohexanecarbaldehyde (2043-61-0) → ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid methyl ester (750594-83-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 84 percent / PPh₃; Et₃N / CH₂Cl₂ / 7 h / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

2.2: 5.56 g / tetrahydrofuran; hexane / 18 h / -78 - 20 °C

3.1: 91 percent / Red-Al / tetrahydrofuran; toluene / 15 h / Heating

4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

4.2: tetrahydrofuran; hexane / 2 h / 0 - 20 °C

5.1: t-BuOK; s-BuLi / cyclohexane / 2.5 h / -78 - -50 °C

5.2: CuCN / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

5.3: 80 percent / tetrahydrofuran; cyclohexane / 4 h / -78 - 20 °C

6.1: 100 percent / FeCl₃ / diethyl ether / 15 h / 20 °C

7.1: 96 percent / K₂CO₃ / methanol / 16 h / 20 °C

8.1: 89 percent / Jones reagent / acetone / 1 h / 20 °C

9.1: DPPA; Et₃N / toluene / 1 h / Heating

9.2: 69 percent / methanol / 1 h / Heating

10.1: O₃; sudan III / CH₂Cl₂ / -78 °C

10.2: 81 percent / NaBH₄ / methanol / 15 h / 20 °C

With n-butyllithium; jones reagent; oil scarlet; diphenyl-phosphinic acid; potassium tert-butylate; sec.-butyllithium; iron(III) chloride; potassium carbonate; ozone; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; acetone; toluene; 9.1: Curtius rearrangement;

DOI:10.1021/ol048936q

upstream raw materials:

{(S)-1-Cyclohexyl-2-[(2S,5R)-2-isopropyl-5-methyl-cyclohex-(E)-ylidene]-ethyl}-carbamic acid methyl ester

1,1-dibromo-2-cyclohexylethene

cyclohexanecarbaldehyde

(1S,2S,5R)-1-Cyclohexylethynyl-2-isopropyl-5-methyl-cyclohexanol