2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

Base Information

• Chemical Name: 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol
• CAS No.: 218912-12-0
• Molecular Formula: C₁₈H₂₉Br₂N₃O₂Si
• Molecular Weight: 507.341

Synonyms:2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

Chemical Property of 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

Chemical Property:

Purity/Quality:

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Technology Process of 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol

There total 8 articles about 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol 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: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-1-[3,5-Dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethane-1,2-diol (218912-11-9) → 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol (218912-12-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 5h;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

methyl 3,5-dibromo-4-aminobenzoate (3282-10-8) → 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol (218912-12-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

2.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

3.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

4.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

5.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

6.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; AD-α; water; pyridinium chlorochromate; sodium nitrite; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Reduction / 2.1: Diazotization / 2.2: Substitution / 3.1: Oxidation / 4.1: Condensation / 5.1: Addition / 6.1: Etherification;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethanol (218912-12-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / SOCl₂ / 2 h / Heating

2.1: 98 percent / Br₂; AcOH / 0.5 h / 25 °C

3.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

4.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

5.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

6.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

7.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

8.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; AD-α; water; bromine; acetic acid; pyridinium chlorochromate; sodium nitrite; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Esterification / 2.1: Bromination / 3.1: Reduction / 4.1: Diazotization / 4.2: Substitution / 5.1: Oxidation / 6.1: Condensation / 7.1: Addition / 8.1: Etherification;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-1-[3,5-Dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethane-1,2-diol

methyl 3,5-dibromo-4-aminobenzoate

4-amino-benzoic acid

Downstream raw materials:

C₅₈H₇₉Br₂ClN₈O₁₁Si

(2S,3R)-2-[(R)-2-{(R)-2-tert-Butoxycarbonylamino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetylamino}-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester

{2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester

2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethylamine

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