(S)-(-)-1-Boc-2-pyrrolidinemethanol

Base Information

• Chemical Name: (S)-(-)-1-Boc-2-pyrrolidinemethanol
• CAS No.: 69610-40-8
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.266
• Hs Code.: 29339900
• Mol file: 69610-40-8.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (S)-;(2S)-1-(tert-Butoxycarbonyl)-2-pyrrolidinemethanol;(2S)-2-Hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester;(2S)-Hydroxymethylpyrrolidine-1-carboxylicacid tert-butyl ester;(S)-(+)-N-Boc-prolinol;(S)-(-)-1-(tert-Butoxycarbonyl)-2-pyrrolidinemethanol;(S)-1-BOC-2-Pyrrolidinemethanol;(S)-2-(Hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester;(S)-N-tert-Butoxycarbonyl-2-pyrrolidinemethanol;(S)-tert-Butyl2-(hydroxymethyl)pyrrolidine-1-carboxylate;1-BOC-2-(S)-Pyrrolidinemethanol;BOC-L-prolinol;Boc-(S)-(-)-2-pyrrolidinemethanol;N-[(tert-Butoxy)carbonyl]-L-prolinol;tert-Butyl(2S)-2-(Hydroxymethyl)-1-pyrrolidinecarboxylate;

Chemical Property of (S)-(-)-1-Boc-2-pyrrolidinemethanol

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0.000241mmHg at 25°C
• Melting Point: 62-64 °C(lit.)
• Refractive Index: -55 ° (C=5, MeOH)
• Boiling Point: 289.5 °C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 128.9 °C
• PSA: 49.77000
• Density: 1.084 g/cm₃
• LogP: 1.31610
• Storage Temp.: Store at 0°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: insoluble

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-L-prolinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Building block for novel nicotinic acetylcholine receptor ligands with cognition-enhancing properties. Used in the synthesis of chiral β-amino sulfides and β-amino thiols.

Technology Process of (S)-(-)-1-Boc-2-pyrrolidinemethanol

There total 69 articles about (S)-(-)-1-Boc-2-pyrrolidinemethanol 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: 100.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/cmdc.201400045

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8)

Guidance literature:

With triethylamine; In ethyl acetate; at 0 - 20 ℃; for 11.5h;

Reference yield: 97.0%

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetasy.2006.05.002

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

di-tert-butyl dicarbonate

(S)-1-Pyrrolidin-2-yl-methanol

(S)-N-(tert-butoxycarbonyl)proline methyl ester

Downstream raw materials:

(S)-2-(bromomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine

tert-butyl (S)-2-vinylpyrrolidine-1-carboxylate

tert-butyl p-methoxybenzyl ether

(S)-tert-butyl 2-((3-fluorophenoxy)methyl)pyrrolidine-1-carboxylate

Refernces

Pyrrolidine-pyridine base catalysts for the enantioselective Michael addition of ketones to chalcones

10.1016/j.tet.2009.09.001

The research focuses on the development of pyrrolidine-pyridine base organocatalysts for the enantioselective Michael addition of ketones to chalcones, a carbon-carbon bond-forming reaction crucial in organic synthesis. The purpose of this study was to overcome the limitations of previous organocatalysts, such as long reaction times, high catalyst loading, and the need for large excesses of ketones, which can increase costs and limit pharmaceutical applications. The researchers synthesized a series of pyrrolidine-pyridine organocatalysts using Boc-L-prolinol as the starting material and tested their effectiveness in the asymmetric Michael addition. The catalyst 3a was found to be highly effective, yielding products with excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 100% ee). The main advantages of this catalyst include ease of synthesis and the use of a small excess of ketones (5 equiv). The reactions were carried out under mild conditions, and various ketones were found to react with chalcones to afford 1,5-dicarbonyl compounds with high enantioselectivity and diastereoselectivity. The chemicals used in the process include cyclohexanone, chalcone 5a, and the synthesized catalysts 3a, 3b, 3c, 3d, and 3e, among others.