tert-Butyl (3-(hydroxymethyl)pyridin-2-yl)carbamate

Base Information

• Chemical Name: tert-Butyl (3-(hydroxymethyl)pyridin-2-yl)carbamate
• CAS No.: 877593-11-8
• Molecular Formula: C₁₁H₁₆N₂O₃
• Molecular Weight: 224.26
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30470035
• Nikkaji Number: J2.281.246G
• Wikidata: Q72480368
• Mol file: 877593-11-8.mol

Synonyms:877593-11-8;tert-Butyl (3-(hydroxymethyl)pyridin-2-yl)carbamate;(3-HYDROXYMETHYLPYRIDIN-2-YL)CARBAMIC ACID TERT-BUTYL ESTER;(3-Hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester;Tert-butyl N-[3-(hydroxymethyl)pyridin-2-yl]carbamate;Carbamic acid, [3-(hydroxymethyl)-2-pyridinyl]-, 1,1-dimethylethyl ester;tert-butyl [3-(hydroxymethyl)pyridin-2-yl]carbamate;DTXSID30470035;KSYLRXQTEZEGQP-UHFFFAOYSA-N;AKOS015838127;SB80068;DS-10702;FT-0648743;EN300-6197443;A862427;tert-Butyl(3-(hydroxymethyl)pyridin-2-yl)carbamate

Chemical Property of tert-Butyl (3-(hydroxymethyl)pyridin-2-yl)carbamate

Chemical Property:

• PSA: 71.45000
• LogP: 1.99390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 224.11609238
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

98%min ^*data from raw suppliers

(3-Hydroxymethylpyridin-2-yl)carbamicacidtert-butylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=C(C=CC=N1)CO
• Uses: (3-Hydroxymethylpyridin-2-yl)carbamic acid tert-butyl ester

Technology Process of tert-Butyl (3-(hydroxymethyl)pyridin-2-yl)carbamate

There total 4 articles about tert-Butyl (3-(hydroxymethyl)pyridin-2-yl)carbamate 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: 65.0%

methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate (877593-10-7) → 2-(tert-butoxycarbonyl)amino-3-hydrohymethyl pyridine (877593-11-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1080/00397910500334371

Reference yield:

methyl 3-{[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate (912369-42-7) + 2-tert-butoxycarbonylamino-nicotinic acid methyl ester (873460-09-4) → 2-(tert-butoxycarbonyl)amino-3-hydrohymethyl pyridine (877593-11-8) + N-[2-(hydroxymethyl)pyridin-3-yl]carbamic acid tert-butyl ester (824429-51-8)

Guidance literature:

methyl 3-{[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate; 2-tert-butoxycarbonylamino-nicotinic acid methyl ester; With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 4h;

With water; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethyl acetate;

Reference yield:

2-aminopyridin-3-carboxylic acid (5345-47-1) → 2-(tert-butoxycarbonyl)amino-3-hydrohymethyl pyridine (877593-11-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / sulfuric acid / 20 h / Heating

2: 75 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 36 h / 20 °C

3: 65 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; sulfuric acid; In tetrahydrofuran; dichloromethane;

DOI:10.1080/00397910500334371

upstream raw materials:

methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate

2-aminopyridin-3-carboxylic acid

methyl 2-aminonicotinate

methyl 3-{[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate

Downstream raw materials:

2-(4-Methoxyphenyl)<1H>-pyrrolo<2,3-b>pyridine

2-(4-Chloroyphenyl)<1H>-pyrrolo<2,3-b>pyridine

2-phenyl-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 Krasavin, Mikhail,Shkavrov, Sergey,Kravchenko, Dmitry. "Preparation and chemical behavior of 2-(tert-butoxycarbonyl)amino-3- bromomethyl pyridine, a novel alkylating agent". . p. 181 - 186. Retrieved 2007/10/03.