(R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol

Base Information

• Chemical Name: (R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol
• CAS No.: 1044740-40-0
• Molecular Formula: C₁₃H₁₆F₃NO
• Molecular Weight: 259.271
• Mol file: 1044740-40-0.mol

Synonyms:(R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol

Chemical Property of (R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol

There total 8 articles about (R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol 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:

(2S)-1-triphenylmethyl-2-pyrrolidinecarboxylic acid (13515-74-7) → (R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol (1044740-40-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 °C / Inert atmosphere

3.1: cesium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / methanol; water / 1.5 h / 20 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 3.5 h / Reflux; Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; water; 2.1: |Swern Oxidation;

DOI:10.1021/acs.orglett.5b01084

Reference yield:

(2S)-1-triphenylmethyl-2-pyrrolidinemethanol (179918-60-6) → (R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol (1044740-40-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

1.2: 1.5 h / -78 °C / Inert atmosphere

2.1: cesium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride / methanol; water / 1.5 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 3.5 h / Reflux; Inert atmosphere

With hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: |Swern Oxidation;

DOI:10.1021/acs.orglett.5b01084

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (R)-2-[(S)-1-benzyl-2-pyrrolidinyl]-1,1,1-trifluoro-2-ethanol (1044740-40-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: thionyl chloride / 24 h / 20 °C / Inert atmosphere

2.1: triethylamine / chloroform / 18 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

4.2: 1.5 h / -78 °C / Inert atmosphere

5.1: cesium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

6.1: hydrogenchloride / methanol; water / 1.5 h / 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 3.5 h / Reflux; Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; 4.1: |Swern Oxidation;

DOI:10.1021/acs.orglett.5b01084

upstream raw materials:

(trifluoromethyl)trimethylsilane

(2S)-1-benzylpirrolidine-2-carbaldehyde

(2S)-1-triphenylmethyl-2-pyrrolidinecarboxylic acid

(2S)-1-triphenylmethyl-2-pyrrolidinemethanol