(1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide

Base Information

• Chemical Name: (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide
• CAS No.: 1415961-21-5
• Molecular Formula: C₁₂H₂₃NO₂
• Molecular Weight: 213.32
• Mol file: 1415961-21-5.mol

Synonyms:(1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide

Chemical Property of (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide

There total 5 articles about (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide 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: 99.0%

(1S,2S,4R)-2-(dimethylamino)-1-methyl-4-(1-methylethenyl)cyclohexanol (78478-85-0) → (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide (1415961-21-5)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 20 ℃; for 2h; Cooling with ice;

DOI:10.1016/j.tetlet.2012.10.080

Reference yield:

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide (1415961-21-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / -5 - 20 °C

2: water / 18 h / 20 °C / Reflux

3: dihydrogen peroxide / water; acetonitrile / 2 h / 20 °C / Cooling with ice

With dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid; In chloroform; water; acetonitrile;

DOI:10.1016/j.tetlet.2012.10.080

Reference yield:

(4R)-limonene 1,2-epoxide (1195-92-2) → (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide (1415961-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1: water / 18 h / 20 °C / Reflux

2: dihydrogen peroxide / water; acetonitrile / 2 h / 20 °C / Cooling with ice

With dihydrogen peroxide; In water; acetonitrile;

DOI:10.1016/j.tetlet.2012.10.080

upstream raw materials:

D-limonene

(4R)-limonene 1,2-epoxide

(1S,2S,4R)-2-(dimethylamino)-1-methyl-4-(1-methylethenyl)cyclohexanol

(1S,2R,4R)-limonene-1,2-epoxide

Downstream raw materials:

[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-4-pentylbenzene

(1S,4R)-p-mentha-2,8-dien-1-ol

diethyl 2-[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-5-pentylphenyl phosphate

Refernces

• 1、 Wilkinson, Shane M.,Price, Jason,Kassiou, Michael. "Improved accessibility to the desoxy analogues of Δ9- tetrahydrocannabinol and cannabidiol". . p. 52 - 54. Retrieved 2013/02/22.