methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate

Base Information

• Chemical Name: methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate
• CAS No.: 288848-27-1
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 288848-27-1.mol

Synonyms:methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate

Chemical Property of methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate

There total 7 articles about methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate 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%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylic acid (288848-25-9) → methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate (288848-27-1)

Guidance literature:

With potassium hydroxide; In diethyl ether; ethanol; at 20 ℃; for 1h;

DOI:10.1021/jo991773c

Reference yield:

methyl 2-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]acetate (52305-35-8) → methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate (288848-27-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / pyridinium p-toluenesulfonate / benzene / 4 h / Heating

2: 85 percent / LiBH₄ / tetrahydrofuran / Heating

3: 90 percent / NaH / dimethylformamide / 72 h / 20 °C

4: 98 percent / pyridinium p-toluenesulfonate / acetone / 8 h / Heating

5: 41 percent / aq. NaOBr / dioxane / 0 - 20 °C

6: 92 percent / KOH / diethyl ether; ethanol / 1 h / 20 °C

With potassium hydroxide; lithium borohydride; sodium hypobromide; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone; benzene; 1: Condensation / 2: Reduction / 3: Alkylation / 4: Hydrolysis / 5: Oxidation / 6: Methylation;

DOI:10.1021/jo991773c

Reference yield:

(1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid (473-72-3,17879-35-5,61376-92-9,61826-55-9,64396-97-0,127062-09-3,52305-34-7) → methyl (1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylate (288848-27-1)

Guidance literature:

Multi-step reaction with 7 steps

1: KOH / diethyl ether; ethanol / 1 h / 20 °C

2: 81 percent / pyridinium p-toluenesulfonate / benzene / 4 h / Heating

3: 85 percent / LiBH₄ / tetrahydrofuran / Heating

4: 90 percent / NaH / dimethylformamide / 72 h / 20 °C

5: 98 percent / pyridinium p-toluenesulfonate / acetone / 8 h / Heating

6: 41 percent / aq. NaOBr / dioxane / 0 - 20 °C

7: 92 percent / KOH / diethyl ether; ethanol / 1 h / 20 °C

With potassium hydroxide; lithium borohydride; sodium hypobromide; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone; benzene; 1: Methylation / 2: Condensation / 3: Reduction / 4: Alkylation / 5: Hydrolysis / 6: Oxidation / 7: Methylation;

DOI:10.1021/jo991773c

upstream raw materials:

diazomethane

(1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanecarboxylic acid

methyl 2-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]acetate

(1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid

Downstream raw materials:

methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

(1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanocarbaldehyde

(1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutylmethanol