(1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one

Base Information

• Chemical Name: (1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one
• CAS No.: 223786-81-0
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333
• Mol file: 223786-81-0.mol

Synonyms:(1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one

Chemical Property of (1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one

There total 7 articles about (1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one 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: 92.0%

p-methoxybenzyl chloride (824-94-2) + (1S,4S,5S)-5-Hydroxymethyl-bicyclo[2.2.1]heptan-2-one (148616-71-1) → (1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one (223786-81-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 23 ℃; for 2.5h;

DOI:10.1016/S0040-4039(99)00040-4

Reference yield:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) → (1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one (223786-81-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

2: 91 percent / mCPBA / CH₂Cl₂ / 1.5 h / -10 - 23 °C

3: 99 percent / Dess-Martin reagent / CH₂Cl₂ / 17 h / 23 °C

4: 98 percent / SmI₂ / tetrahydrofuran; methanol / 0.67 h / -78 °C

5: 92 percent / NaH,; TBAI / dimethylformamide / 2.5 h / 23 °C

With lithium aluminium tetrahydride; samarium diiodide; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Cyclization / 3: Oxidation / 4: Reduction / 5: Alkylation;

DOI:10.1016/S0040-4039(99)00040-4

Reference yield:

(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol (95-12-5,13360-81-1,15507-06-9,42070-72-4,67505-46-8,67671-05-0,67671-06-1,69831-10-3,42070-82-6) → (1S,4S,5S)-5-(4-Methoxy-benzyloxymethyl)-bicyclo[2.2.1]heptan-2-one (223786-81-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / mCPBA / CH₂Cl₂ / 1.5 h / -10 - 23 °C

2: 99 percent / Dess-Martin reagent / CH₂Cl₂ / 17 h / 23 °C

3: 98 percent / SmI₂ / tetrahydrofuran; methanol / 0.67 h / -78 °C

4: 92 percent / NaH,; TBAI / dimethylformamide / 2.5 h / 23 °C

With samarium diiodide; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Oxidation / 3: Reduction / 4: Alkylation;

DOI:10.1016/S0040-4039(99)00040-4

upstream raw materials:

p-methoxybenzyl chloride

(1S,4S,5S)-5-Hydroxymethyl-bicyclo[2.2.1]heptan-2-one

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol

Downstream raw materials:

(1S,5S,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one

(1R,5R,6S)-6-(4-Methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octane-3,4-dione

(1R,4R,5R,6S)-4-Hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one

(1R,4S,5R,6S)-4-Allyl-4-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-oxa-bicyclo[3.2.1]octan-3-one