(5R)-5-(phenylMethyl)-2-Pyrrolidinone

Base Information

• Chemical Name: (5R)-5-(phenylMethyl)-2-Pyrrolidinone
• CAS No.: 63328-11-0
• Molecular Formula: C11H13NO
• Molecular Weight: 175.23
• DSSTox Substance ID: DTXSID001288738
• Nikkaji Number: J1.340.340F
• Mol file: 63328-11-0.mol

Synonyms:2-Pyrrolidinone,5-(phenylmethyl)-,(R);

Chemical Property of (5R)-5-(phenylMethyl)-2-Pyrrolidinone

Chemical Property:

• Melting Point: 56-58℃
• Boiling Point: 362.0±11.0 °C(Predicted)
• PKA: 16.62±0.40(Predicted)
• PSA: 32.59000
• Density: 1.098±0.06 g/cm3(Predicted)
• LogP: 1.78360
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 175.099714038
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC1CC2=CC=CC=C2
• Isomeric SMILES: C1CC(=O)N[C@H]1CC2=CC=CC=C2

Technology Process of (5R)-5-(phenylMethyl)-2-Pyrrolidinone

There total 19 articles about (5R)-5-(phenylMethyl)-2-Pyrrolidinone 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: 96.0%

(R)-2-benzyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (128811-42-7) → (5R)-5-benzylpyrrolidin-2-one (63328-11-0)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/jacs.6b12113

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (5R)-5-benzylpyrrolidin-2-one (63328-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1: DMAP; DCC / CH₂Cl₂ / -5 °C

2: 13.530 g / NaBH₄; AcOH / CH₂Cl₂ / 18 h / -5 °C

3: toluene / 5 h / 110 °C

4: 3.989 g / TFA / CH₂Cl₂ / 4 h / 20 °C

With dmap; sodium tetrahydroborate; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1021/jo050645n

Reference yield:

(R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester (197006-05-6) → (5R)-5-benzylpyrrolidin-2-one (63328-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 5 h / 110 °C

2: 3.989 g / TFA / CH₂Cl₂ / 4 h / 20 °C

With trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1021/jo050645n

upstream raw materials:

<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate

phenyllithium

(5R)-5-(bromomethyl)pyrrolidin-2-one

methyl (E,4S)-4-(((benzyloxy)carbonyl)amino)-5-phenylpent-2-enoate

Downstream raw materials:

(5S)-5-benzyl-3,3-bis(phenylseleno)pyrrolidin-2-one

(3R,5S)-5-benzyl-3-phenylselenopyrrolidin-2-one

(3S,5S)-5-benzyl-3-phenylselenopyrrolidin-2-one

(5R)-1,5-dibenzylpyrrolidin-2-one