methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

Base Information

• Chemical Name: methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate
• CAS No.: 303191-12-0
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.396

Synonyms:methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

Chemical Property of methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

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Technology Process of methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

There total 42 articles about methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate 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:

(2S,4aR,5S)-5-Benzyloxy-7-hydroxy-2-(2-methoxymethoxy-ethyl)-hexahydro-pyrido[1,2-b][1,2]oxazin-8-one → methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate (303191-12-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: imidazole / dimethylformamide / 42 h / 20 °C

2.1: tetrahydrofuran / 0.17 h / 0 °C

2.2: 82 percent / NaBH₃CN; AcOH / tetrahydrofuran / 1 h / 0 °C

3.1: Zn; AcOH / H₂O / 1 h / 60 °C / 7

4.1: 90 percent / KOH; K₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

5.1: NaH; imidazole / tetrahydrofuran / 1 h / Heating

5.2: 98 percent / tetrahydrofuran / 0.5 h / Heating

6.1: 95 percent / tributyltinhydride; 2,2-azobisisobutyronitrile / benzene / 3 h / Heating

7.1: 81 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 3 h / Heating

8.1: 95 percent / H₂ / Pd(OH)2 / methanol / 1.5 h

9.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

10.1: 87 percent / AcOH; piperidine / benzene / 1 h / Heating

11.1: pyridinium dichromate / dimethylformamide / 12 h / 20 °C

12.1: 75 percent / diethyl ether / 0 °C

13.1: 84 percent / thionyl chloride; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

14.1: Bu₄NF / tetrahydrofuran / 120 h / 20 °C

With piperidine; 1H-imidazole; potassium hydroxide; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; zinc; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 9.1: Swern oxidation;

DOI:10.1021/jo001589n

Reference yield:

(2S,4aR,5S,7S,8S)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(2-methoxymethoxy-ethyl)-8-methyl-octahydro-pyrido[1,2-b][1,2]oxazine → methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate (303191-12-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Zn; aq. AcOH / 60 °C

2.2: aq. KOH

3.1: NaH; imidazole

3.2: 98 percent / tetrahydrofuran

4.1: Bu₃SnH; AIBN / benzene / Heating

5.1: PPTS / 2-methyl-propan-2-ol / Heating

6.1: H₂ / Pd(OH)2 / methanol

7.1: (COCl)2; DMSO; Et₃N / -89 - 0 °C

8.1: 87 percent / piperidine; AcOH / benzene / Heating

9.1: PDC / dimethylformamide

10.1: diethyl ether

11.1: 84 percent / SOCl₂; Et₃N

12.1: Bu₄NF / tetrahydrofuran / 20 °C

13.1: Bu₄NF / tetrahydrofuran / 120 h / 20 °C

With piperidine; 1H-imidazole; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; zinc; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.1: reductive ring cleavage / 2.1: Acylation / 2.2: Hydrolysis / 3.1: Addition / 3.2: Methylation / 4.1: deoxygenation / 5.1: ether cleavage / 6.1: Hydrogenolysis / 7.1: Swern oxidation / 8.1: Cyclization / 9.1: Oxidation / 10.1: Methylation / 11.1: Dehydration / 12.1: desilylation; epimerization / 13.1: epimerization;

DOI:10.1021/ol000153r

Reference yield:

(S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol → methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate (303191-12-0)

Guidance literature:

Multi-step reaction with 12 steps

1.2: aq. KOH

2.1: NaH; imidazole

2.2: 98 percent / tetrahydrofuran

3.1: Bu₃SnH; AIBN / benzene / Heating

4.1: PPTS / 2-methyl-propan-2-ol / Heating

5.1: H₂ / Pd(OH)2 / methanol

6.1: (COCl)2; DMSO; Et₃N / -89 - 0 °C

7.1: 87 percent / piperidine; AcOH / benzene / Heating

8.1: PDC / dimethylformamide

9.1: diethyl ether

10.1: 84 percent / SOCl₂; Et₃N

11.1: Bu₄NF / tetrahydrofuran / 20 °C

12.1: Bu₄NF / tetrahydrofuran / 120 h / 20 °C

With piperidine; 1H-imidazole; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.1: Acylation / 1.2: Hydrolysis / 2.1: Addition / 2.2: Methylation / 3.1: deoxygenation / 4.1: ether cleavage / 5.1: Hydrogenolysis / 6.1: Swern oxidation / 7.1: Cyclization / 8.1: Oxidation / 9.1: Methylation / 10.1: Dehydration / 11.1: desilylation; epimerization / 12.1: epimerization;

DOI:10.1021/ol000153r

upstream raw materials:

methyl (2S,3S,5S,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-enoate

ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-en-ol

Downstream raw materials:

methyl (2S,3S,5R,8aR)-1-benzoyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

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