(2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester
CAS No.:612067-29-5
Molecular Formula:C₃₅H₄₃NO₄Si
Molecular Weight:569.816
Hs Code.:

(2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

Synonyms:(2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

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Technology Process of (2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

There total 14 articles about (2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl 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:

: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(1,2-dihydroxy-ethyl)-6-methyl-1,3a,8,8a-tetrahydro-2H-3-aza-cyclopenta[a]indene-3-carboxylic acid tert-butyl ester

: 612067-29-5
(2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 2h;

Reference yield:

: 7697-28-1
4-bromo-3-methylbenzoic acid

: 612067-29-5
(2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 96 percent / lithium aluminium hydride / diethyl ether / 2 h / 20 °C

2.1: phosphorus tribromide / diethyl ether / 1 h / Heating

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: tetrahydrofuran / 2 h / -78 °C

4.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C

5.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: aluminium trichloride / CH₂Cl₂ / 1 h / 0 °C

7.1: 98 percent / lithium hydroxide / tetrahydrofuran; H₂O / 8 h / 20 °C

8.1: 90 percent / BH₃*Me₂S / tetrahydrofuran / 5 h / 20 °C

9.1: 84 percent / tetrakis(triphenylphosphino)palladium / toluene / 24 h / Heating

10.1: 97 percent / potassium hydroxide / methanol / 4 h / Heating

11.1: 95 percent / CH₂Cl₂ / 4 h / 20 °C

12.1: 92 percent / imidazole / tetrahydrofuran / 20 °C

13.1: 40 mg / sodium periodate; osmium tetraoxide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; lithium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; aluminium trichloride; dimethylsulfide borane complex; phosphorus tribromide; lithium triethylborohydride; triethylamine; lithium hexamethyldisilazane; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 6.1: intramolecular Friedel-Crafts cyclization / 9.1: Stille coupling;

Reference yield:

: 27561-51-9
1-bromo-4-(bromomethyl)-2-methylbenzene

: 612067-29-5
(2S,3aS,8aR)-2-(tert-butyldiphenylsilanyloxymethyl)-5-formyl-6-methyl-1,3a,8,8a-tetrahydro-2H-3-azacyclopenta[a]indene-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 2 h / -78 °C

2.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C

3.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: aluminium trichloride / CH₂Cl₂ / 1 h / 0 °C

5.1: 98 percent / lithium hydroxide / tetrahydrofuran; H₂O / 8 h / 20 °C

6.1: 90 percent / BH₃*Me₂S / tetrahydrofuran / 5 h / 20 °C

7.1: 84 percent / tetrakis(triphenylphosphino)palladium / toluene / 24 h / Heating

8.1: 97 percent / potassium hydroxide / methanol / 4 h / Heating

9.1: 95 percent / CH₂Cl₂ / 4 h / 20 °C

10.1: 92 percent / imidazole / tetrahydrofuran / 20 °C

11.1: 40 mg / sodium periodate; osmium tetraoxide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; lithium hydroxide; sodium periodate; osmium(VIII) oxide; aluminium trichloride; dimethylsulfide borane complex; lithium triethylborohydride; triethylamine; lithium hexamethyldisilazane; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 4.1: intramolecular Friedel-Crafts cyclization / 7.1: Stille coupling;