1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-5-(1-hydroxyethyl)-, phenylmethyl ester, (R)-

Base Information

• Chemical Name: 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-5-(1-hydroxyethyl)-, phenylmethyl ester, (R)-
• CAS No.: 183866-61-7
• Molecular Formula: C15H19NO3
• Molecular Weight: 261.321
• Mol file: 183866-61-7.mol

Synonyms:

Chemical Property of 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-5-(1-hydroxyethyl)-, phenylmethyl ester, (R)-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-5-(1-hydroxyethyl)-, phenylmethyl ester, (R)-

There total 6 articles about 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-5-(1-hydroxyethyl)-, phenylmethyl ester, (R)- 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%

(1R)-1-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)ethanol (72504-66-6) + benzyl chloroformate (501-53-1,94274-21-2) → 5-((R)-1-Hydroxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (183866-61-7)

Guidance literature:

In dichloromethane; for 9h; Heating;

DOI:10.1016/S0957-4166(97)00071-2

Reference yield:

1-Benzyl-3-((R)-1-hydroxy-ethyl)-pyridinium; chloride → 5-((R)-1-Hydroxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (183866-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / NaBH₄ / methanol / 12 h / 25 °C

2: 50 percent / CH₂Cl₂ / 9 h / Heating

With sodium tetrahydroborate; In methanol; dichloromethane;

DOI:10.1016/S0957-4166(97)00071-2

Reference yield:

methyl-3-pyridylketone (350-03-8) → 5-((R)-1-Hydroxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester (183866-61-7)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄ / methanol / 2 h / Ambient temperature

2: 40 h / Ambient temperature; Pseudomonas sp. lipase

3: K₂CO₃ / methanol / 1 h / Ambient temperature

4: 2.) NaBH₄ / 1.) MeOH, 80 deg C, 3 h, 2.) MeOH, RT, 12 h

5: CH₂Cl₂ / Heating

With sodium tetrahydroborate; potassium carbonate; In methanol; dichloromethane;

DOI:10.1016/0957-4166(96)00359-X

upstream raw materials:

(1R)-1-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)ethanol

benzyl chloroformate

methyl-3-pyridylketone

1-(3-Pyridyl)ethanol

Downstream raw materials:

(R)-3-Eth-(Z)-ylidene-4-(1H-indol-2-ylmethyl)-piperidine-1-carboxylic acid benzyl ester

(R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

Refernces

• 1、 Amat, Mercedes,Coll, Ma-Dolors,Passarella, Daniele,Bosch, Joan. "An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline". . p. 2775 - 2778. Retrieved 2007/10/03.