Benzyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: Benzyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS No.: 124391-76-0
• Molecular Formula: C13H17NO3
• Molecular Weight: 235.283
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10452657
• Wikidata: Q82273415
• Mol file: 124391-76-0.mol

Synonyms:124391-76-0;(S)-benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate;BENZYL (3S)-3-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE;(S)-1-Cbz-beta-Prolinol;(S)-1-Cbz-3-hydroxymethylpyrrolidine;(S)-1-Cbz-3-(hydroxymethyl)pyrrolidine;MFCD06858680;1-PYRROLIDINECARBOXYLIC ACID, 3-(HYDROXYMETHYL)-, PHENYLMETHYL ESTER, (3S)-;1-Cbz-3-hydroxymethyl-pyrrolidine;(S)-1-Cbz-b-prolinol;SCHEMBL541346;DTXSID10452657;ZRMWRJLLAVAFQP-LBPRGKRZSA-N;ZEA39176;(S)-3-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER;AKOS015856183;AKOS015911904;CS-W003363;AS-80086;TS-00661;A5707;EN300-7419603;Q-102183;(S)-benzyl3-(hydroxymethyl)pyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylicacid,3-(hydroxymethyl)-,phenylmethyl ester,(3S)-

Chemical Property of Benzyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• Boiling Point: 381.969 °C at 760 mmHg
• Flash Point: 184.809 °C
• PSA: 49.77000
• Density: 1.196 g/cm³
• LogP: 1.57530
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 235.12084340
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

Benzyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1CO)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CN(C[C@H]1CO)C(=O)OCC2=CC=CC=C2

Technology Process of Benzyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 10 articles about Benzyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate 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%

(S)-(-)-3-(hydroxymethyl)pyrrolidine (110013-19-9) + benzyl chloroformate (501-53-1,94274-21-2) → -(+)-methanol (124391-76-0)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1021/jo9701905

Reference yield:

(S)-(-)-N-benzylpyrrolidine-2-methanol hydrochloride (78914-69-9) → -(+)-methanol (124391-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂ / Pd/C / ethanol / 24 h

2: 90 percent / aq. K₂CO₃ / tetrahydrofuran / 4 h / 0 °C

With hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1021/jo9701905

Reference yield:

(R)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one (172796-28-0) → -(+)-methanol (124391-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / LAH / tetrahydrofuran / 0 deg C to reflux

2: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 85 percent / Et₃N / dioxane / 12 h / Heating

4: 95 percent / H₂ / Pd/C / methanol / 24 h

5: 95 percent / H₂ / Pd/C / ethanol / 24 h

6: 90 percent / aq. K₂CO₃ / tetrahydrofuran / 4 h / 0 °C

With dmap; lithium aluminium tetrahydride; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane;

DOI:10.1021/jo9701905

upstream raw materials:

1-carboxybenzyl-3-pyrrolidine

chlorobromomethane

(S)-(-)-3-(hydroxymethyl)pyrrolidine

benzyl chloroformate

Downstream raw materials:

(S)-(+)-3-pyrrolidinecarboxylic acid

(S)-3-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-pyrrolidine-1-carboxylic acid benzyl ester

(S)-3-(4-Benzyloxycarbonylamino-2-fluoro-phenoxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester

N-{(S)-3-[3-Fluoro-4-((S)-1-pyrrolidin-3-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Refernces

• 1、 -. "Method of treating addiction or dependence using a ligand for a monoamine receptor or transporter". . . Retrieved 2008/06/13.
• 2、 Mazzini,Lebreton,Alphand,Furstoss. "Enantiodivergent chemoenzymatic synthesis of (R)- and (S)-β-proline in high optical purity". . p. 5215 - 5218. Retrieved 2007/10/03.