(1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone

Base Information

Chemical Name:(1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone
CAS No.:149818-81-5
Molecular Formula:C₁₅H₁₉NO₂
Molecular Weight:245.321
Hs Code.:

Synonyms:(1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone

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Chemical Property of (1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone

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Technology Process of (1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone

There total 4 articles about (1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone 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: 90.0%

: 149818-80-4
(1S,1'R,2R,2'S)-2-<2'-<(Boc)amino>-1'-hydroxy-3'-phenylpropyl>cyclopentanecarboxylic acid lactone

: 149818-81-5
(1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1021/jo00069a024

Reference yield:

: 72155-45-4
Boc-L-phenylalaninal

: 149818-81-5
(1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 30 percent / 1.) LDA / tetrahydrofuran / 1.) -78 deg C, 1.5 h, 2.) -78 deg C, 5 min

2: 1.) LiCN, 2.) SmI₂, t-BuOH / 1.) THF, 0 deg C, 20 min, 2.) THF, 0 deg C, 1 h

3: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

With samarium diiodide; lithium cyanide; trifluoroacetic acid; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00069a024

Reference yield:

: 120-92-3
cyclopentanone

: 149818-81-5
(1S,1'R,2R,2'S)-2-(2'-Amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 30 percent / 1.) LDA / tetrahydrofuran / 1.) -78 deg C, 1.5 h, 2.) -78 deg C, 5 min

2: 1.) LiCN, 2.) SmI₂, t-BuOH / 1.) THF, 0 deg C, 20 min, 2.) THF, 0 deg C, 1 h

3: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

With samarium diiodide; lithium cyanide; trifluoroacetic acid; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00069a024