(3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:1160437-95-5
Molecular Formula:C₃₇H₅₅N₃O₈
Molecular Weight:669.859
Hs Code.:

(3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of (3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

There total 14 articles about (3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl 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:

: 1147886-82-5
(R)-2-ethoxy-1-propanol

: 1160437-95-5
(3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydride / N,N-dimethyl-formamide; oil / 19 h / -10 - 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 - 2 h / 20 °C

3: dmap; triethylamine / dichloromethane / 2 - 18 h / 0 - 20 °C

4: sodium azide / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 2 h / 50 °C

5: hydrogen / palladium 10% on activated carbon / methanol / 15 - 20 °C

6: triethylamine / dichloromethane / 1 h

With dmap; sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; dichloromethane; N,N-dimethyl-formamide; oil;

Reference yield:

: 303043-57-4
(3R,4R,5S)-3-hydroxy-5-hydroxymethyl-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

: 1160437-95-5
(3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

2.1: 1,3-bis-(diphenylphosphino)propane / palladium diacetate / N,N-dimethyl-formamide / 0.33 h / 20 °C

2.2: 4 h / 70 °C / 3750.38 Torr

2.3: 12 h / 70 °C / 3750.38 Torr

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; oil / 19 h / -10 - 20 °C

5.1: sodium hydroxide; water / tetrahydrofuran / 16 h / 90 °C

5.2: pH 3

6.1: borane-THF / tetrahydrofuran / 1 - 3 h / 20 °C

7.1: methanesulfonyl chloride; triethylamine / dichloromethane / 16 h / 20 °C

8.1: sodium hydride / N,N-dimethyl-formamide; oil / 19 h / -10 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 - 2 h / 20 °C

10.1: dmap; triethylamine / dichloromethane / 2 - 18 h / 0 - 20 °C

11.1: sodium azide / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 2 h / 50 °C

12.1: hydrogen / palladium 10% on activated carbon / methanol / 15 - 20 °C

13.1: triethylamine / dichloromethane / 1 h

With 1H-imidazole; dmap; sodium hydroxide; sodium azide; borane-THF; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; methanesulfonyl chloride; triethylamine; palladium diacetate; palladium 10% on activated carbon; In tetrahydrofuran; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; dichloromethane; N,N-dimethyl-formamide; oil;

Reference yield:

: 1160437-83-1
(3R,4R,5S)-3-hydroxy-5-hydroxymethyl-4-(4-methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

: 1160437-95-5
(3R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formylaminomethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; oil / 19 h / -10 - 20 °C

3.1: sodium hydroxide; water / tetrahydrofuran / 16 h / 90 °C

3.2: pH 3

4.1: borane-THF / tetrahydrofuran / 1 - 3 h / 20 °C

5.1: methanesulfonyl chloride; triethylamine / dichloromethane / 16 h / 20 °C

6.1: sodium hydride / N,N-dimethyl-formamide; oil / 19 h / -10 - 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 - 2 h / 20 °C

8.1: dmap; triethylamine / dichloromethane / 2 - 18 h / 0 - 20 °C

9.1: sodium azide / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 2 h / 50 °C

10.1: hydrogen / palladium 10% on activated carbon / methanol / 15 - 20 °C

11.1: triethylamine / dichloromethane / 1 h

With 1H-imidazole; dmap; sodium hydroxide; sodium azide; borane-THF; tetrabutyl ammonium fluoride; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; methanesulfonyl chloride; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; dichloromethane; N,N-dimethyl-formamide; oil;