ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Base Information

• Chemical Name: ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate
• CAS No.: 1416960-94-5
• Molecular Formula: C₁₅H₂₇NO₄
• Molecular Weight: 285.384
• Mol file: 1416960-94-5.mol

Synonyms:ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Chemical Property of ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

There total 13 articles about ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate 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: 95.0%

ethyl trans-4-[1-(tert-butoxycarbonyl)-(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate (1416960-86-5) → ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate (1416960-94-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2012.11.003

Reference yield:

1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3R)-methoxypyrrolidine (1416960-93-4) → ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate (1416960-94-5)

Guidance literature:

Multi-step reaction with 8 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 0 - 20 °C

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 7 h / Reflux

3: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 22 h

4: Rh/Al₂O₃; trifluoroacetic acid; hydrogen / methanol / 15 h / 10?atm

5: sodium hydrogencarbonate / acetonitrile; water / 48 h / 20 °C

6: sodium ethanolate / ethanol / 16 h / Inert atmosphere; Reflux

7: potassium carbonate / 2 h / 60 °C

8: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With di-isopropyl azodicarboxylate; 10 wt% Pd(OH)2 on carbon; Rh/Al₂O₃; tetrabutyl ammonium fluoride; hydrogen; sodium ethanolate; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile; 2: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2012.11.003

Reference yield:

1-benzyloxycarbonyl-(3R)-methoxy-(2R)-pyrrolidinemethanol (1416960-83-2) → ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate (1416960-94-5)

Guidance literature:

Multi-step reaction with 7 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 7 h / Reflux

2: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 22 h

3: Rh/Al₂O₃; trifluoroacetic acid; hydrogen / methanol / 15 h / 10?atm

4: sodium hydrogencarbonate / acetonitrile; water / 48 h / 20 °C

5: sodium ethanolate / ethanol / 16 h / Inert atmosphere; Reflux

6: potassium carbonate / 2 h / 60 °C

7: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With di-isopropyl azodicarboxylate; 10 wt% Pd(OH)2 on carbon; Rh/Al₂O₃; hydrogen; sodium ethanolate; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile; 1: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2012.11.003

upstream raw materials:

1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3R)-hydroxypyrrolidine

1-benzyloxycarbonyl-(3R)-methoxy-(2R)-pyrrolidinemethanol

1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3R)-methoxypyrrolidine

Ethyl 4-hydroxybenzoate

Downstream raw materials:

ethyl trans-4-[1-[[7-fluoro-2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl]acetyl]-(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate