(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

Base Information

Chemical Name:(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine
CAS No.:151256-36-9
Molecular Formula:C₂₄H₃₆N₄O₃Si
Molecular Weight:456.66
Hs Code.:

Synonyms:(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

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Chemical Property of (8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

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Technology Process of (8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

There total 15 articles about (8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine 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: 98.0%

: 100-39-0
benzyl bromide

: 151256-48-3
(8R)-6-(tert-Butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

: (8R)-1-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

: 151256-36-9
(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

Guidance literature:: With triethylamine; In tetrahydrofuran; for 3h; Yields of byproduct given; Heating;
DOI:10.1021/jo00074a041

Reference yield: 97.0%

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

: 151256-33-6
(8R)-3-Benzyl-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

: 151256-36-9
(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

Guidance literature:: In methanol; Ambient temperature;
DOI:10.1021/jo00074a041

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 151256-36-9
(8R)-3-Benzyl-6-(tert-butoxycarbonyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

Guidance literature:: Multi-step reaction with 12 steps

1: 99 percent / imidazole / dimethylformamide / 96 h / Ambient temperature

2: 98 percent / aq. LiOH / dioxane / 3 h / 5 °C

3: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) ammonia / 1.) THF, -23 deg C, 90 s, 2.) -23 deg C, 2 h

4: 99 percent / p-toluenesulfonyl chloride, pyridine / CH₂Cl₂ / 96 h / Ambient temperature

5: 93 percent / trifluoroacetic acid / CH₂Cl₂; H₂O / 0.75 h / 0 °C

6: 97 percent / 2 h / Heating

7: 97 percent / 5-Angstroem molecular sieves / acetonitrile / 2 h / Heating

8: 88 percent / 5-Angstroem molecular sieves, trifluoroacetic acid / 3 h / Heating

9: 99 percent / triethylamine, 1,3-propanedithiol / methanol / Ambient temperature

10: 99 percent / methanol / Ambient temperature

11: 99.4 percent / t-BuOK, t-BuOH / tetrahydrofuran / 0.02 h / Ambient temperature

12: 98 percent / triethylamine / tetrahydrofuran / 3 h / Heating

With 4-methyl-morpholine; pyridine; 1H-imidazole; 1.3-propanedithiol; lithium hydroxide; 5A molecular sieve; potassium tert-butylate; ammonia; triethylamine; p-toluenesulfonyl chloride; trifluoroacetic acid; tert-butyl alcohol; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00074a041