(S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile

Base Information

• Chemical Name: (S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile
• CAS No.: 148766-02-3
• Molecular Formula: C₁₁H₁₉NO
• Molecular Weight: 181.278
• Mol file: 148766-02-3.mol

Synonyms:(S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile

Chemical Property of (S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile

There total 5 articles about (S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile 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: 77.0%

(4R,4aR,5S,8aR)-4,5-Dimethyl-3-oxoperhydroisochroman (130607-97-5) → (S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile (148766-02-3)

Guidance literature:

With dimethylaluminium amide; In xylene; at 100 ℃;

DOI:10.1016/S0040-4039(00)60377-5

Reference yield:

(R)-2-((1S,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionic acid tert-butyl ester → (S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile (148766-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Ambient temperature

2: 77 percent / Me₂AlNH₂ / xylene / 100 °C

With dimethylaluminium amide; potassium tert-butylate; In tetrahydrofuran; xylene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)60377-5

Reference yield:

(2E,7E)-(R)-2,4-Dimethyl-nona-2,7-dienedioic acid 1-tert-butyl ester 9-methyl ester → (S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile (148766-02-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / Li(s-Bu)3BH (L-Selectride) / tetrahydrofuran / -80 - -20 °C

2: 97 percent / NaAl(CH₃OCH₂CH₂O)2H₂ (Red-Al)

3: 64 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Ambient temperature

4: 77 percent / Me₂AlNH₂ / xylene / 100 °C

With dimethylaluminium amide; potassium tert-butylate; L-Selectride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; xylene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)60377-5

upstream raw materials:

(S)-2-[(1R,2S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-cyclohexyl]-propionitrile

(4R,4aR,5S,8aR)-4,5-Dimethyl-3-oxoperhydroisochroman

(1S,2R,3R)-2-((R)-1-tert-Butoxycarbonyl-ethyl)-3-methyl-cyclohexanecarboxylic acid methyl ester

Downstream raw materials:

2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2R,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-3-hydroxy-propionic acid methyl ester

(Z)-2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2S,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-acrylic acid methyl ester

(E)-2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2S,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-acrylic acid methyl ester

(Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester