5-(Benzyloxy)-1-(pyrrolidin-1-YL)pentan-1-one

Base Information

• Chemical Name: 5-(Benzyloxy)-1-(pyrrolidin-1-YL)pentan-1-one
• CAS No.: 117959-71-4
• Molecular Formula: C16H23NO2
• Molecular Weight: 261.364
• DSSTox Substance ID: DTXSID80557527
• Wikidata: Q82439474
• Mol file: 117959-71-4.mol

Synonyms:117959-71-4;5-(BENZYLOXY)-1-(PYRROLIDIN-1-YL)PENTAN-1-ONE;DTXSID80557527

Chemical Property of 5-(Benzyloxy)-1-(pyrrolidin-1-YL)pentan-1-one

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 261.172878976
• Heavy Atom Count: 19
• Complexity: 256

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)C(=O)CCCCOCC2=CC=CC=C2

Technology Process of 5-(Benzyloxy)-1-(pyrrolidin-1-YL)pentan-1-one

There total 1 articles about 5-(Benzyloxy)-1-(pyrrolidin-1-YL)pentan-1-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:

pyrrolidine (123-75-1) + 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + benzyl chloride (100-44-7) → 5-Benzyloxy-1-pyrrolidin-1-yl-pentan-1-one (117959-71-4)

Guidance literature:

With potassium hydroxide; 1,1'-carbonyldiimidazole; Yield given. Multistep reaction; 1.) toluene, reflux;

DOI:10.1021/ja00234a046

Reference yield: 87.0%

1-(carboxymethoxy)cyclopentadiene (25662-28-6) + (E)-9-iodo-2,6-dimethylnona-2,6-diene (22339-13-5) + 5-Benzyloxy-1-pyrrolidin-1-yl-pentan-1-one (117959-71-4) → (1R,2S)-2-[4-Benzyloxy-1-(pyrrolidine-1-carbonyl)-butyl]-1-((E)-4,8-dimethyl-nona-3,7-dienyl)-cyclopentanecarboxylic acid methyl ester

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - -25 ℃;

DOI:10.1021/ja00234a046

Reference yield:

5-Benzyloxy-1-pyrrolidin-1-yl-pentan-1-one (117959-71-4) → <1α(R*S*),2α,2(E)>-(+/-)-2-(4,8-Dimethyl-3,7-nonadienyl)-2-(hydroxymethyl)-β-<3-(phenylmethoxy)propyl>cyclopentaneethanol (117959-74-7,118015-94-4,138604-15-6,138604-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / LDA / tetrahydrofuran / -78 - -25 °C

2: 1.) DIBAL; 2.) NaOH / 2.) EtOH, H₂O, 95 deg C

3: 96 percent / LiAlH₄

With sodium hydroxide; lithium aluminium tetrahydride; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/ja00234a046

upstream raw materials:

pyrrolidine

3,4,5,6-tetrahydro-2H-pyran-2-one

benzyl chloride

Downstream raw materials:

2-[4-Benzyloxy-1-(pyrrolidine-1-carbonyl)-butyl]-1-(4-methyl-pent-3-enyl)-cyclopentanecarboxylic acid methyl ester

(1R,2S)-2-[(S)-4-Benzyloxy-1-(pyrrolidine-1-carbonyl)-butyl]-1-(4-methyl-pent-3-enyl)-cyclopentanecarboxylic acid methyl ester

(1R,2R)-2-[4-Benzyloxy-1-(pyrrolidine-1-carbonyl)-butyl]-1-((E)-4,8-dimethyl-nona-3,7-dienyl)-cyclopentanecarboxylic acid methyl ester

Methyl <1α,1(E),2α(S^*)>-(+/-)-1-(4,8-Dimethyl-3,7-nonadienyl)-2-<4-(phenylmethoxy)-1-(1-pyrrolidinylcarbonyl)butyl>cyclopentanecarboxylate