benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate

Base Information

• Chemical Name: benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate
• CAS No.: 953787-28-5
• Molecular Formula: C₁₆H₂₂N₂O₃
• Molecular Weight: 290.362
• Mol file: 953787-28-5.mol

Synonyms:benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate

Chemical Property of benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate

There total 1 articles about benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate 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: 93.4%

(2R,5R)-2,5-dimethylpyrrolidine (62617-70-3) + N-(Benzyloxycarbonyl)glycine (1138-80-3) → benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate (953787-28-5)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ol701704h

Reference yield: 99.0%

benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate (953787-28-5) → benzyl (2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-thioxoethyl)-carbamate (1355611-20-9)

Guidance literature:

With Lawessons reagent; sodium hydrogencarbonate; In toluene; at 120 ℃; for 3h;

DOI:10.1021/jo201753q

Reference yield:

benzyl 2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-oxoethylcarbamate (953787-28-5) → benzyl 1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-1-oxo-3-vinylhexan-2-ylcarbamate

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-di-tert-butylpyridine / 4 h / 20 °C

2: n-butyllithium / hexane / 4 h / -35 - 20 °C

With n-butyllithium; 2,6-di-tert-butyl-pyridine; In hexane;

DOI:10.1021/ol701704h

upstream raw materials:

(2R,5R)-2,5-dimethylpyrrolidine

N-(Benzyloxycarbonyl)glycine

Downstream raw materials:

(2S,3S)-2-(benzyloxycarbonylamino)-3-methylpent-4-enoic acid

benzyl (2R,3R)-1-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-3-methyl-1-thioxopent-4-en-2-ylcarbamate

(S)-methyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate

(S)-ethyl 2-((S)-1-(benzyloxycarbonylamino)-2-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)-2-thioxoethyl)but-3-enoate