(1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol

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Chemical Name:(1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol
CAS No.:872033-14-2
Molecular Formula:C₁₄H₂₂N₂O₂
Molecular Weight:250.341
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol

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Technology Process of (1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol

There total 6 articles about (1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol 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: 89.0%

: 872033-14-2
(1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol

Guidance literature:

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 872033-14-2
(1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - -30 °C / Inert atmosphere

2.1: potassium carbonate / acetonitrile / 0.25 h / 25 °C / Inert atmosphere

2.2: 48 h

3.1: L-Selectride / tetrahydrofuran; methanol / 3 h / -78 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

5.1: 5%-palladium/activated carbon; hydrogen / methanol / 16 h / 25 °C

6.1: trifluoroacetic acid / dichloromethane / 25 °C

With n-butyllithium; 5%-palladium/activated carbon; hydrogen; L-Selectride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm3001136

Reference yield:

: 176504-90-8
dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate

: 872033-14-2
(1R,2R,3S)-3-amino-4-phenyl-1-[(R)-pyrrolidin-2-yl]butane-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / acetonitrile / 0.25 h / 25 °C / Inert atmosphere

1.2: 48 h

2.1: L-Selectride / tetrahydrofuran; methanol / 3 h / -78 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

4.1: 5%-palladium/activated carbon; hydrogen / methanol / 16 h / 25 °C

5.1: trifluoroacetic acid / dichloromethane / 25 °C

With 5%-palladium/activated carbon; hydrogen; L-Selectride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm3001136