methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate

Base Information

Chemical Name:methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate
CAS No.:460054-25-5
Molecular Formula:C₂₉H₃₇NO₄Si
Molecular Weight:491.703
Hs Code.:

Synonyms:methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate

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Chemical Property of methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate

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Technology Process of methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate

There total 12 articles about methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate 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:

: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-7-trimethylsilanyloxy-3,4,4a,5,8,8a-hexahydro-2H-quinoline-1-carboxylic acid methyl ester

: 460054-25-5
methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate

Guidance literature:: With palladium diacetate; In acetonitrile; at 20 ℃; for 40h;
DOI:10.1021/jo025929b

Reference yield:

: (2S,3S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-carboxymethyl-3-vinyl-piperidine-1-carboxylic acid methyl ester

: 460054-25-5
methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 741 mg / triethylamine / CH₂Cl₂ / 16 h / 20 °C

2.1: 96 percent / tetrahydrofuran / 1 h / 20 °C

3.1: 79 percent / OsO₄; sodium metaperiodate / dioxane; H₂O / 8 h / 20 °C

4.1: 52 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 48 h / Heating

5.1: CuI / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

5.2: HMPA / tetrahydrofuran; diethyl ether / 1 h / -78 °C

6.1: 74 mg / Pd(OAc)2 / acetonitrile / 40 h / 20 °C

With palladium diacetate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; acetonitrile; benzene; 6.1: Ito-Saegusa oxidation;
DOI:10.1021/jo025929b

Reference yield:

: 442202-05-3
dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

: 460054-25-5
methyl (2S,4aS,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-2H-quinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: MeLi / diethyl ether / 0.5 h / 0 °C

1.2: CuI / diethyl ether / 0.33 h / -35 °C

1.3: 96 percent / diethyl ether / 1 h / -30 °C

2.1: LiOH*H₂O / methanol; H₂O / 2 h / Heating

3.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

4.1: diethyl ether / 15 h / 20 °C

5.1: 2.4 g / silver benzoate; Et₃N / 9 h / 20 °C

6.1: LiOH*H₂O / methanol; H₂O / 1 h / Heating

7.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

7.2: 741 mg / triethylamine / CH₂Cl₂ / 16 h / 20 °C

8.1: 96 percent / tetrahydrofuran / 1 h / 20 °C

9.1: 79 percent / OsO₄; sodium metaperiodate / dioxane; H₂O / 8 h / 20 °C

10.1: 52 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 48 h / Heating

11.1: CuI / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C

11.2: HMPA / tetrahydrofuran; diethyl ether / 1 h / -78 °C

12.1: 74 mg / Pd(OAc)2 / acetonitrile / 40 h / 20 °C

With palladium diacetate; lithium hydroxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; methyllithium; silver benzoate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetonitrile; benzene; 12.1: Ito-Saegusa oxidation;
DOI:10.1021/jo025929b