[(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile

Base Information

• Chemical Name: [(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile
• CAS No.: 220467-06-1
• Molecular Formula: C₁₈H₂₃NO
• Molecular Weight: 269.387
• Mol file: 220467-06-1.mol

Synonyms:[(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile

Chemical Property of [(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile

There total 3 articles about [(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile 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: 93.0%

sodium cyanide (143-33-9,25596-52-5) + [2-((1R,2R)-2-Bromomethyl-2-methyl-3-methylene-cyclopentyl)-ethoxymethyl]-benzene (220466-90-0) → [(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile (220467-06-1)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; at 100 ℃; for 48h;

DOI:10.1016/S0040-4039(98)02535-0

Reference yield:

(1R,2R)-2-Bromomethyl-1-(2-hydroxyethyl)-2-methyl-3-methylenecyclopentane (99277-05-1) → [(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile (220467-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / KN(TMS)2 / tetrahydrofuran / 0 °C

2: 93 percent / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / 48 h / 100 °C

With potassium hexamethylsilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane;

DOI:10.1016/S0040-4039(98)02535-0

Reference yield:

(1R,2R)-2-Bromomethyl-1-methoxycarbonylmethyl-2-methyl-3-methylenecyclopentane (104758-32-9) → [(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetonitrile (220467-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / LiAlH₄ / diethyl ether / 1.5 h / -60 °C

2: 93 percent / KN(TMS)2 / tetrahydrofuran / 0 °C

3: 93 percent / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / 48 h / 100 °C

With lithium aluminium tetrahydride; potassium hexamethylsilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether;

DOI:10.1016/S0040-4039(98)02535-0

upstream raw materials:

sodium cyanide

[2-((1R,2R)-2-Bromomethyl-2-methyl-3-methylene-cyclopentyl)-ethoxymethyl]-benzene

(1R,2R)-2-Bromomethyl-1-(2-hydroxyethyl)-2-methyl-3-methylenecyclopentane

(1R,2R)-2-Bromomethyl-1-methoxycarbonylmethyl-2-methyl-3-methylenecyclopentane

Downstream raw materials:

[(1R,2R)-2-(2-Benzyloxy-ethyl)-1-methyl-5-methylene-cyclopentyl]-acetaldehyde

(5E,10E)-9-(tert-Butyl-diphenyl-silanyloxy)-12-[(1R,2R)-2-(2-hydroxy-ethyl)-2-methyl-3-methylene-cyclopentyl]-6,10-dimethyl-dodeca-5,10-dien-2-ol

{(1R,2R)-2-[(2E,7E)-4-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-11-oxo-dodeca-2,7-dienyl]-1-methyl-5-methylene-cyclopentyl}-acetaldehyde

tert-Butyl-diphenyl-((5E,10E,14E)-(3aR,16aR)-6,10,14,16a-tetramethyl-1-methylene-1,2,3,3a,4,7,8,9,12,13,16,16a-dodecahydro-cyclopentacyclopentadecen-7-yloxy)-silane