(S)-N-Boc-2-Hydroxymethylmorpholine

Base Information

• Chemical Name: (S)-N-Boc-2-Hydroxymethylmorpholine
• CAS No.: 135065-76-8
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• Hs Code.: 2934999090
• European Community (EC) Number: 696-348-1
• DSSTox Substance ID: DTXSID80363726
• Nikkaji Number: J2.163.296A
• Wikidata: Q72449578
• Mol file: 135065-76-8.mol

Synonyms:4-Morpholinecarboxylicacid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (S)-;(2S)-2-(Hydroxymethyl)morpholine-4-carboxylicacid tert-butyl ester;(S)-2-Hydroxymethylmorpholine-4-carboxylic acidtert-butyl ester;

Chemical Property of (S)-N-Boc-2-Hydroxymethylmorpholine

Chemical Property:

• Appearance/Colour: White crystal powder
• Vapor Pressure: 2.53E-05mmHg at 25°C
• Melting Point: 60-62 °C
• Refractive Index: 1.474
• Boiling Point: 320.7 °C at 760 mmHg
• PKA: 14.36±0.10(Predicted)
• Flash Point: 147.8 °C
• PSA: 59.00000
• Density: 1.118 g/cm³
• LogP: 0.55250
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 217.13140809
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

(S)-tert-Butyl2-(hydroxymethyl)morpholine-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCOC(C1)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCO[C@@H](C1)CO
• Uses: (S)-N-Boc-2-hydroxymethylmorpholine is used as a pharmaceutical intermediate.

Technology Process of (S)-N-Boc-2-Hydroxymethylmorpholine

There total 12 articles about (S)-N-Boc-2-Hydroxymethylmorpholine 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%

(S)-2,4-morpholinedicarboxylic acid 4-(1,1-dimethylethyl)ester (868689-63-8) → tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate (135065-76-8)

Guidance literature:

With diborane; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

Reference yield: 97.7%

(S)-2-benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester (911223-10-4) → tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate (135065-76-8)

Guidance literature:

With hydrogenchloride; hydrogen; 1% Pd/C; In ethanol; water; at 70 ℃;

Reference yield: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-morpholin-2-ylmethanol (132073-83-7) → tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate (135065-76-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 16h;

upstream raw materials:

di-tert-butyl dicarbonate

(S)-morpholin-2-ylmethanol

(6S)-6-(hydroxymethyl)morpholin-3-one

(-)-2-chloro-N-((S)-2,3-dihydroxypropyl)acetamide

Downstream raw materials:

(S)-4-tert-butoxycarbonyl-2-p-nitrobenzenesulfonyloxymethylmorpholine

(S)-(+)-2-formylmorpholine-4-carboxylic acid tert-butyl ester

(S)-2-{4-[3-chloro-4-(3-fluoro-benzyloxy)-5 phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethoxy methyl}-morpholine-4-carboxylic acid tert-butyl ester

(R)-2-formylmorpholin-4-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "COMPOUNDS". Page/Page column 123. . Retrieved 2015/09/23.
• 2、 Fritz, Sven P.,Mumtaz, Amara,Yar, Muhammad,McGarrigle, Eoghan M.,Aggarwal, Varinder K.. "Sulfinamides as highly effective amine protecting groups and their use in the conversion of Amino alcohols into morpholines". experimental part. p. 3156 - 3164. Retrieved 2011/06/28.