5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester

Base Information

Chemical Name:5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester
CAS No.:128228-76-2
Molecular Formula:C₃₅H₃₅NO₇
Molecular Weight:581.665
Hs Code.:

5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benz<e>indole, (R)-(-)-O-acetylmandelate ester

Synonyms:5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester

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Chemical Property of 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester

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Technology Process of 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester

There total 11 articles about 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate 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:

: 51019-43-3
(R)-(-)-O-acetylmandelic acid

: 122745-39-5
5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole

: 128228-76-2
5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester

: 128228-77-3
5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetyl mandelate ester

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 24 ℃; for 1h;
DOI:10.1016/S0040-4039(00)94629-X

Reference yield:

: 13802-40-9
1-Methoxy-3-nitronaphthalene

: 128228-76-2
5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester

Guidance literature:: Multi-step reaction with 9 steps

1: 91 percent / 48percent aq. HBr / acetic acid / 6 h / Heating

2: 97 percent / K₂CO₃, Bu₄NI / dimethylformamide / 3 h / 25 °C

3: 99 percent / Al(Hg) / tetrahydrofuran; H₂O / 2.5 h / 25 °C

4: 96 percent / dioxane / 3 h / 95 °C

5: 98 percent / N-bromosuccinimide, H₂SO₄ / tetrahydrofuran / 5 h / -60 °C

6: 1.) NaH / 1.) THF, DMF, 24 deg C, 30 min, 2.) THF, DMF, toluene, 24 deg C, 3h

7: tri-n-butyltin hydride, AIBN / benzene / 1 h / Heating

8: 1.) borane methyl sulfide, 2.) 30percent aq. H₂O₂, 2N aq. NaOH / 1.) THF, 24 deg C, 3h, 2.) 24 deg C, 1h, then 45 deg C, 20 min

9: 131 mg / (3-(dimethylamino)propyl)ethylcarbodiimide hydrochloride / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 24 °C

With sodium hydroxide; aluminum amalgam; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; sulfuric acid; hydrogen bromide; dihydrogen peroxide; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00310a013

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 128228-76-2
5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetylmandelate ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / dioxane / 3 h / 95 °C

2: 98 percent / N-bromosuccinimide, H₂SO₄ / tetrahydrofuran / 5 h / -60 °C

3: 1.) NaH / 1.) THF, DMF, 24 deg C, 30 min, 2.) THF, DMF, toluene, 24 deg C, 3h

4: tri-n-butyltin hydride, AIBN / benzene / 1 h / Heating

5: 1.) borane methyl sulfide, 2.) 30percent aq. H₂O₂, 2N aq. NaOH / 1.) THF, 24 deg C, 3h, 2.) 24 deg C, 1h, then 45 deg C, 20 min

6: 131 mg / (3-(dimethylamino)propyl)ethylcarbodiimide hydrochloride / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 24 °C

With sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; In tetrahydrofuran; 1,4-dioxane; dichloromethane; benzene;
DOI:10.1021/jo00310a013