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

Base Information

• Chemical Name: Benzoic acid (8R,8aS)-3,3-dimethyl-5-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-8-yl ester
• CAS No.: 168772-36-9
• Molecular Formula: C₁₆H₁₇NO₄
• Molecular Weight: 287.315
• Mol file: 168772-36-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about Benzoic acid (8R,8aS)-3,3-dimethyl-5-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-8-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: 86.0%

2,2-dimethoxy-propane (77-76-9) + Benzoic acid (2S,3R)-2-hydroxymethyl-6-oxo-1,2,3,6-tetrahydro-pyridin-3-yl ester (168772-35-8) → Benzoic acid (8R,8aS)-3,3-dimethyl-5-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-8-yl ester (168772-36-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; at 78 ℃;

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

Reference yield:

Benzoic acid (Z)-(R)-1-((S)-1-amino-2-hydroxy-ethyl)-3-ethoxycarbonyl-allyl ester (1027557-52-3) → Benzoic acid (8R,8aS)-3,3-dimethyl-5-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-8-yl ester (168772-36-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 86 percent / pyridinium p-toluenesulfonate / benzene / 78 °C

With pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In ethyl acetate; benzene;

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 (8R,8aS)-3,3-dimethyl-5-oxo-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-8-yl ester (168772-36-9)

Guidance literature:

Multi-step reaction with 5 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

5: 86 percent / pyridinium p-toluenesulfonate / benzene / 78 °C

With quinoline; Lindlar's catalyst; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; trifluoroacetic acid; In diethyl ether; water; ethyl acetate; benzene;

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

upstream raw materials:

2,2-dimethoxy-propane

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

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