Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester
• CAS No.: 168772-35-8
• Molecular Formula: C₁₃H₁₃NO₄
• Molecular Weight: 247.251
• Mol file: 168772-35-8.mol

Synonyms:Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester

Chemical Property of Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester

There total 4 articles about Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester 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:

Benzoic acid (Z)-(R)-1-((S)-1-amino-2-hydroxy-ethyl)-3-ethoxycarbonyl-allyl ester (1027557-52-3) → Benzoic acid (1S,5S,8R)-3-oxo-6-oxa-2-aza-bicyclo[3.2.1]oct-8-yl ester + Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester (168772-35-8)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; for 15h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/0957-4166(95)00129-D

Reference yield:

(S)-3-((R)-3-Ethoxycarbonyl-1-hydroxy-prop-2-ynyl)-1-oxa-4-aza-spiro[4.5]decane-4-carboxylic acid tert-butyl ester → Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester (168772-35-8)

Guidance literature:

Multi-step reaction with 4 steps

1: -50 - 20 °C

2: H₂, Lindlar's catalyst, quinolin / ethyl acetate / 760 Torr / Ambient temperature

3: TFA / diethyl ether; H₂O / 1 h / Ambient temperature

4: aq. NaHCO₃ / ethyl acetate / 15 h / Ambient temperature

With quinoline; Lindlar's catalyst; hydrogen; sodium hydrogencarbonate; trifluoroacetic acid; In diethyl ether; water; ethyl acetate;

DOI:10.1016/0957-4166(95)00129-D

Reference yield:

(S)-3-((Z)-(R)-1-Benzoyloxy-3-ethoxycarbonyl-allyl)-1-oxa-4-aza-spiro[4.5]decane-4-carboxylic acid tert-butyl ester (168772-34-7) → Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester (168772-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / diethyl ether; H₂O / 1 h / Ambient temperature

2: aq. NaHCO₃ / ethyl acetate / 15 h / Ambient temperature

With sodium hydrogencarbonate; trifluoroacetic acid; In diethyl ether; water; ethyl acetate;

DOI:10.1016/0957-4166(95)00129-D

upstream raw materials:

Benzoic acid (Z)-(R)-1-((S)-1-amino-2-hydroxy-ethyl)-3-ethoxycarbonyl-allyl ester

(S)-3-((Z)-(R)-1-Benzoyloxy-3-ethoxycarbonyl-allyl)-1-oxa-4-aza-spiro[4.5]decane-4-carboxylic acid tert-butyl ester

(S)-3-((R)-1-Benzoyloxy-3-ethoxycarbonyl-prop-2-ynyl)-1-oxa-4-aza-spiro[4.5]decane-4-carboxylic acid tert-butyl ester

Downstream raw materials:

Benzoic acid (8R,8aS)-3,3-dimethyl-5-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-8-yl ester