(S)--ALLYL-PROLINE HYDROCHLORIDE

Base Information

• Chemical Name: (S)--ALLYL-PROLINE HYDROCHLORIDE
• CAS No.: 129704-91-2
• Molecular Formula: C8H13NO2 · HCl
• Molecular Weight: 191.66
• Mol file: 129704-91-2.mol

Synonyms:(s)-α-allyl-proline hydrochloride;α-allyl-d-proline hydrochloride;(S)-a-Allylproline·HCl;α-Allyl-D-proline hydrochloride, (S)-2-Allyl-2-pyrrolidinecarboxylic acid hydrochloride;D-Proline, 2-(2-propenyl)-, hydrochloride (9CI)

Chemical Property of (S)--ALLYL-PROLINE HYDROCHLORIDE

Chemical Property:

• Vapor Pressure: 0.000202mmHg at 25°C
• Boiling Point: 304.3°C at 760 mmHg
• Flash Point: 137.8°C
• PSA: 49.33000
• LogP: 1.90010

Purity/Quality:

99%, ^*data from raw suppliers

(S)-α-Allyl-proline hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-Alpha-allyl-proline Hydrochloride is used in the synthesis of Avrainvillamide and Stephacidins, analogs of these natural products are evaluated as anticancer agents.

Technology Process of (S)--ALLYL-PROLINE HYDROCHLORIDE

There total 2 articles about (S)--ALLYL-PROLINE HYDROCHLORIDE 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: 50.0%

(2R,5R)-5-(2-propenyl)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]octane-4-one (220200-87-3) → (R)-2-allylpyrrolidine-2-carboxylic acid hydrochloride (129704-91-2) + (R)-methyl 2-allylpyrrolidine-2-carboxylate (389127-43-9) + (R)-methyl 2-allylpyrrolidene-2-carboxylate hydrochloride

Guidance literature:

With hydrogenchloride; In methanol; for 4h; Reflux;

DOI:10.1002/chem.201700747

Reference yield:

(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one (118916-60-2,97538-67-5) → (R)-2-allylpyrrolidine-2-carboxylic acid hydrochloride (129704-91-2) + (R)-methyl 2-allylpyrrolidine-2-carboxylate (389127-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 3 h / -78 °C

2.1: hydrogenchloride / methanol / 4 h / Reflux

With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; methanol;

DOI:10.1002/chem.201700747

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (R)-2-allylpyrrolidine-2-carboxylic acid hydrochloride (129704-91-2) → (R)-methyl 2-allylpyrrolidine-2-carboxylate (389127-43-9)

Guidance literature:

In methanol; benzene; at 0 ℃; for 0.5h;

DOI:10.1021/ja061660s

upstream raw materials:

(2R,5R)-5-(2-propenyl)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]octane-4-one

(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

Downstream raw materials:

(R)-methyl 2-allylpyrrolidine-2-carboxylate

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