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

Base Information

Chemical Name:methyl (2S,4aR,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-7-oxo-3,4,4a,8,8a-hexahydro-2H-quinoline-1-carboxylate
CAS No.:460054-11-9
Molecular Formula:C₂₈H₃₅NO₄Si
Molecular Weight:477.676
Hs Code.:

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

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

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

There total 10 articles about methyl (2S,4aR,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-7-oxo-3,4,4a,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: 52.0%

: 460054-09-5
methyl (2S,3R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-3-formyl-2-(2-oxopropyl)piperidine-1-carboxylate

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

: 460054-11-9
methyl (2S,4aR,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-7-oxo-3,4,4a,8,8a-hexahydro-2H-quinoline-1-carboxylate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; for 48h; Heating;
DOI:10.1021/jo025929b

Reference yield:

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

: 460054-11-9
methyl (2S,4aR,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-7-oxo-3,4,4a,8,8a-hexahydro-2H-quinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 4 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

With sodium periodate; osmium(VIII) oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; benzene;
DOI:10.1021/jo025929b

Reference yield:

: 442202-22-4
dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

: 460054-11-9
methyl (2S,4aR,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-7-oxo-3,4,4a,8,8a-hexahydro-2H-quinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

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

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

3.1: diethyl ether / 15 h / 20 °C

4.1: 2.4 g / silver benzoate; Et₃N / 9 h / 20 °C

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

6.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 741 mg / triethylamine / CH₂Cl₂ / 16 h / 20 °C

7.1: 96 percent / tetrahydrofuran / 1 h / 20 °C

8.1: 79 percent / OsO₄; sodium metaperiodate / dioxane; H₂O / 8 h / 20 °C

9.1: 52 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 48 h / Heating

With lithium hydroxide; sodium periodate; osmium(VIII) oxide; 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; benzene;
DOI:10.1021/jo025929b