(R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one

Base Information

• Chemical Name: (R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one
• CAS No.: 911705-78-7
• Molecular Formula: C₃₅H₄₄N₂O₇S
• Molecular Weight: 636.81
• Mol file: 911705-78-7.mol

Synonyms:(R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one

Chemical Property of (R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one

There total 13 articles about (R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one 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:

N-methoxy-2-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-N-methyl-acetamide (911705-80-1) + methylmagnesium bromide (75-16-1) → (R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one (911705-78-7)

Guidance literature:

N-methoxy-2-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-N-methyl-acetamide; methylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 1h;

With potassium hydrogensulfate; In tetrahydrofuran; water;

Reference yield:

(S)-1-(4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine-2-carboxylic acid ethyl ester (911705-05-0) → (R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one (911705-78-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; ethanol; water / 3 - 6 h / 75 °C

2.1: borane-THF / tetrahydrofuran / 2 - 6 h / 40 °C

3.1: trifluorormethanesulfonic acid / dichloromethane / 3 h / -30 - 0 °C

4.1: ammonium cerium(IV) nitrate; water / acetonitrile / 0.5 h / 0 °C

5.1: borane-THF / tetrahydrofuran / 2 - 8 h / 50 °C

6.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

7.2: 0 - 20 °C

8.1: triethylamine / dichloromethane / 1 h / 0 °C

9.1: dimethyl sulfoxide / 4 h / 50 °C

10.1: sodium hydroxide; water / ethanol / 85 °C

10.2: 20 °C

11.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / dichloromethane; ethyl acetate / 1 - 3 h / 20 °C

12.1: tetrahydrofuran / 1 h / 0 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; ammonium cerium(IV) nitrate; trifluorormethanesulfonic acid; water; sodium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;

Reference yield:

4-methoxyphenylboronic acid (5720-07-0) → (R,S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one (911705-78-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; ethanol; water / 3 - 6 h / 75 °C

2.1: borane-THF / tetrahydrofuran / 2 - 6 h / 40 °C

3.1: trifluorormethanesulfonic acid / dichloromethane / 3 h / -30 - 0 °C

4.1: ammonium cerium(IV) nitrate; water / acetonitrile / 0.5 h / 0 °C

5.1: borane-THF / tetrahydrofuran / 2 - 8 h / 50 °C

6.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

7.2: 0 - 20 °C

8.1: triethylamine / dichloromethane / 1 h / 0 °C

9.1: dimethyl sulfoxide / 4 h / 50 °C

10.1: sodium hydroxide; water / ethanol / 85 °C

10.2: 20 °C

11.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / dichloromethane; ethyl acetate / 1 - 3 h / 20 °C

12.1: tetrahydrofuran / 1 h / 0 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; ammonium cerium(IV) nitrate; trifluorormethanesulfonic acid; water; sodium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;

upstream raw materials:

N-methoxy-2-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-N-methyl-acetamide

methylmagnesium bromide

(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-2-carboxylic acid ethyl ester

6-hydroxymethyl-4-(3-methoxy-propyl)-4H-benzo[1,4]oxazin-3-one

Downstream raw materials:

(R,S)-1-methoxy-3-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-2-methyl-propan-2-ol

(S)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-ol

(R)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-ol

6-[(3R,4R,6R)-4-(4-methoxy-phenyl)-6-((R,S)-2-pyrrolidin-1-yl-propyl)-1-(toluene-4-sulfonyl)-piperidin-3-yloxymethyl]-4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazine