(3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one

Base Information

• Chemical Name: (3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one
• CAS No.: 951172-65-9
• Molecular Formula: C₂₄H₂₅N₃O₅
• Molecular Weight: 435.48
• Mol file: 951172-65-9.mol

Synonyms:(3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one

Chemical Property of (3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one

There total 3 articles about (3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-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: 75.0%

1-amino-3-phthalimidopropane trifluoroacetic acid salt + (2S,4S)-3-benzyloxycarbonyl-4-methyl-4-(2-oxoethyl)-2-phenyloxazolidin-5-one (951172-60-4) → (3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one (951172-65-9)

Guidance literature:

With sodium acetate; sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 36h; pH=6.0;

DOI:10.1021/jo071074x

Reference yield:

(2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one (951172-59-1) → (3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one (951172-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone / CH₂Cl₂ / 0.75 h

1.2: 82 percent / dimethyl sulfide / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 75 percent / NaCNBH₃; acetic acid; NaOAc / methanol / 36 h / 20 °C / pH 6.0

With sodium acetate; sodium cyanoborohydride; ozone; acetic acid; In methanol; dichloromethane;

DOI:10.1021/jo071074x

Reference yield:

(S,S)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester (171860-41-6) → (3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-phthalimidopropyl)pyrrolidin-2-one (951172-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.25 h / -78 °C

1.2: 91 percent / tetrahydrofuran / 21 h / -78 - 20 °C

2.1: ozone / CH₂Cl₂ / 0.75 h

2.2: 82 percent / dimethyl sulfide / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 75 percent / NaCNBH₃; acetic acid; NaOAc / methanol / 36 h / 20 °C / pH 6.0

With sodium acetate; sodium cyanoborohydride; ozone; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo071074x

upstream raw materials:

(2S,4S)-3-benzyloxycarbonyl-4-methyl-4-(2-oxoethyl)-2-phenyloxazolidin-5-one

(2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one

(S,S)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

(3R)-3-benzyloxycarbonylamino-3-methyl-1-(3-aminopropyl)pyrrolidine-2-thione