(2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

Base Information

Chemical Name:(2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine
CAS No.:1105510-20-0
Molecular Formula:C₂₈H₃₃BrClFN₂O₂Si
Molecular Weight:592.023
Hs Code.:

Synonyms:(2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

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Chemical Property of (2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

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Technology Process of (2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

There total 8 articles about (2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine 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: 90.0%

: 1105510-17-5
(2R,6S)-4-(2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

: 1105510-20-0
(2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

Guidance literature:: (2R,6S)-4-(2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -70 - 10 ℃; for 0.5h;

With 1,2-dibromo-1,1,2,2-tetrafluoroethane; In tetrahydrofuran; hexane; at -70 ℃;
DOI:10.1021/ol503256h

Reference yield:

: 1105510-12-0
3-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-5-fluoro-pyridine-2-carboxylic acid

: 1105510-20-0
(2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 1 h / 20 °C / Cooling with ice

2.1: lithium borohydride / 1 h

3.1: 1H-imidazole / dichloromethane / 1 h / 0 - 20 °C

4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 - 10 °C

4.2: -70 °C

5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 - 10 °C

5.2: -70 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol503256h

Reference yield:

: 745784-04-7
3,5-difluoropyridine-2-carboxylic acid

: 1105510-20-0
(2R,6S)-4-(6-bromo-2-((tert-butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

Guidance literature:: Multi-step reaction with 6 steps

1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 72 h / 20 °C

2.1: triethylamine / tetrahydrofuran / 1 h / 20 °C / Cooling with ice

3.1: lithium borohydride / 1 h

4.1: 1H-imidazole / dichloromethane / 1 h / 0 - 20 °C

5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 - 10 °C

5.2: -70 °C

6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 - 10 °C

6.2: -70 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol503256h