N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide

Base Information

Chemical Name:N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide
CAS No.:1350705-85-9
Molecular Formula:C₁₉H₃₀N₂O₄Si
Molecular Weight:378.544
Hs Code.:

Synonyms:N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide

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Chemical Property of N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide

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Technology Process of N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide

There total 9 articles about N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide 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:

: 4397-53-9
p-benzyloxybenzaldehyde

: 1350705-85-9
N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: water / 2 h / 90 °C / Inert atmosphere

2.1: tert-butylhypochlorite; sodium hydroxide / propan-1-ol; water / 0.08 h / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

4.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

5.1: N-benzyl-trimethylammonium hydroxide / 8 h / Reflux; Inert atmosphere

6.1: lithium borohydride / methanol; diethyl ether / 4 h / 20 °C / Inert atmosphere

7.1: ytterbium(III) triflate / dichloromethane / 8 h / Inert atmosphere; Reflux

8.1: 6 h / Inert atmosphere; Reflux

With 1H-imidazole; lithium borohydride; tert-butylhypochlorite; 5%-palladium/activated carbon; hydrogen; N-benzyl-trimethylammonium hydroxide; sodium hydroxide; ytterbium(III) triflate; In methanol; propan-1-ol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Michael reaction;
DOI:10.1039/c1ob06320k

Reference yield:

: 1350705-81-5
(2S,3R)-ethyl 3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate

: 1350705-85-9
N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide

Guidance literature:: Multi-step reaction with 5 steps

1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

2: N-benzyl-trimethylammonium hydroxide / 8 h / Reflux; Inert atmosphere

3: lithium borohydride / methanol; diethyl ether / 4 h / 20 °C / Inert atmosphere

4: ytterbium(III) triflate / dichloromethane / 8 h / Inert atmosphere; Reflux

5: 6 h / Inert atmosphere; Reflux

With lithium borohydride; 5%-palladium/activated carbon; hydrogen; N-benzyl-trimethylammonium hydroxide; ytterbium(III) triflate; In methanol; diethyl ether; dichloromethane; 2: Michael reaction;
DOI:10.1039/c1ob06320k

Reference yield:

: 1350705-68-8
ethyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate

: 1350705-85-9
N-((1R,2R)-1-(tert-butyldimethylsilyloxy)-1-(4-(2-cyanoethoxy)-phenyl)-3-hydroxypropan-2-yl)formamide

Guidance literature:: Multi-step reaction with 6 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

2: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / Inert atmosphere

3: N-benzyl-trimethylammonium hydroxide / 8 h / Reflux; Inert atmosphere

4: lithium borohydride / methanol; diethyl ether / 4 h / 20 °C / Inert atmosphere

5: ytterbium(III) triflate / dichloromethane / 8 h / Inert atmosphere; Reflux

6: 6 h / Inert atmosphere; Reflux

With 1H-imidazole; lithium borohydride; 5%-palladium/activated carbon; hydrogen; N-benzyl-trimethylammonium hydroxide; ytterbium(III) triflate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 3: Michael reaction;
DOI:10.1039/c1ob06320k