(3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester
• CAS No.: 141708-15-8
• Molecular Formula: C₂₇H₂₅NO₄
• Molecular Weight: 427.5

Synonyms:(3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

Chemical Property of (3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

There total 3 articles about (3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 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:

benzyl chloroformate (501-53-1,94274-21-2) → (3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester (141708-15-8)

Guidance literature:

Multi-step reaction with 2 steps

2: 1) CuCN / 1) THF, 0 deg C, 5 min, 2) THF, -78 deg C, 1 h

With 1) CuCN;

DOI:10.1021/jo00040a018

Reference yield:

(3S,7aR)-7a-Methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one (137869-70-6,153745-22-3) → (3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester (141708-15-8)

Guidance literature:

Multi-step reaction with 2 steps

2: 1) CuCN / 1) THF, 0 deg C, 5 min, 2) THF, -78 deg C, 1 h

With 1) CuCN;

DOI:10.1021/jo00040a018

Reference yield:

phenyllithium (591-51-5) + (3S,7aR)-7a-Methyl-5-oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester (141708-08-9) → (3S,7aR)-7a-Methyl-5-oxo-3,7-diphenyl-hexahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester (141708-15-8)

Guidance literature:

With 1) CuCN; Yield given. Multistep reaction; 1) THF, 0 deg C, 5 min, 2) THF, -78 deg C, 1 h;

DOI:10.1021/jo00040a018

upstream raw materials:

phenyllithium

(3S,7aR)-7a-Methyl-5-oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester

benzyl chloroformate

(3S,7aR)-7a-Methyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Downstream raw materials:

(S)-2-Methyl-3-phenyl-pyrrolidine

(S)-2-((S)-2-Methyl-3-phenyl-pyrrolidin-1-yl)-2-phenyl-ethanol

(3S,7R,7aR)-7a-Methyl-3,7-diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

(3S,7S,7aR)-7a-Methyl-3,7-diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

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