1-Piperidinecarboxylic acid, 3-[[3,4-dihydro-4-(3-methoxypropyl)-2H-1,4-benzoxazin-6-yl]methoxy]-4- [4-[[(3S)-1-(3-fluorophenyl)-3-pyrrolidinyl]oxy]phenyl]-5-hydroxy-, phenylmethyl ester, (3R,4S,5S)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3-[[3,4-dihydro-4-(3-methoxypropyl)-2H-1,4-benzoxazin-6-yl]methoxy]-4- [4-[[(3S)-1-(3-fluorophenyl)-3-pyrrolidinyl]oxy]phenyl]-5-hydroxy-, phenylmethyl ester, (3R,4S,5S)-
• CAS No.: 873945-20-1
• Molecular Formula: C42H48FN3O7
• Molecular Weight: 725.857
• Mol file: 873945-20-1.mol

Synonyms:

Chemical Property of 1-Piperidinecarboxylic acid, 3-[[3,4-dihydro-4-(3-methoxypropyl)-2H-1,4-benzoxazin-6-yl]methoxy]-4- [4-[[(3S)-1-(3-fluorophenyl)-3-pyrrolidinyl]oxy]phenyl]-5-hydroxy-, phenylmethyl ester, (3R,4S,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3-[[3,4-dihydro-4-(3-methoxypropyl)-2H-1,4-benzoxazin-6-yl]methoxy]-4- [4-[[(3S)-1-(3-fluorophenyl)-3-pyrrolidinyl]oxy]phenyl]-5-hydroxy-, phenylmethyl ester, (3R,4S,5S)-

There total 13 articles about 1-Piperidinecarboxylic acid, 3-[[3,4-dihydro-4-(3-methoxypropyl)-2H-1,4-benzoxazin-6-yl]methoxy]-4- [4-[[(3S)-1-(3-fluorophenyl)-3-pyrrolidinyl]oxy]phenyl]-5-hydroxy-, phenylmethyl ester, (3R,4S,5S)- 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:

benzyl 4-{4-[1-(3-fluorophenyl)pyrrolidin-3-yloxy]phenyl}-3-hydroxy-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]-oxazin-6-ylmethoxy]piperidine-1-carboxylate → benzyl 4-{4-[1-(3-fluorophenyl)pyrrolidin-3-yloxy]phenyl}-3-hydroxy-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]-oxazin-6-ylmethoxy]piperidine-1-carboxylate (873945-20-1)

Guidance literature:

With diisopropyl (E)-azodicarboxylate; triphenylphosphine; benzoic acid; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield:

1-(3-fluorophenyl)pyrrolidin-3-yl p-toluene-4-sulphonate → benzyl 4-{4-[1-(3-fluorophenyl)pyrrolidin-3-yloxy]phenyl}-3-hydroxy-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]-oxazin-6-ylmethoxy]piperidine-1-carboxylate (873945-20-1)

Guidance literature:

Multi-step reaction with 5 steps

1: caesium carbonate / acetonitrile / 2 h / 80 °C

2: sodium hydride / N,N-dimethyl-formamide / 19 h / -10 - 20 °C

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

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

5: diisopropyl (E)-azodicarboxylate; triphenylphosphine; benzoic acid / tetrahydrofuran / 3 h / 20 °C

With borane-THF; tetrabutyl ammonium fluoride; sodium hydride; caesium carbonate; diisopropyl (E)-azodicarboxylate; triphenylphosphine; benzoic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one (615568-17-7) → benzyl 4-{4-[1-(3-fluorophenyl)pyrrolidin-3-yloxy]phenyl}-3-hydroxy-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]-oxazin-6-ylmethoxy]piperidine-1-carboxylate (873945-20-1)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium fluoride; potassium iodide / acetonitrile / 72 h / Heating / reflux

2: thionyl chloride / pyridine; dichloromethane / 1 h / 0 - 20 °C

3: sodium hydride / N,N-dimethyl-formamide / 19 h / -10 - 20 °C

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

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

6: diisopropyl (E)-azodicarboxylate; triphenylphosphine; benzoic acid / tetrahydrofuran / 3 h / 20 °C

With potassium fluoride; thionyl chloride; borane-THF; tetrabutyl ammonium fluoride; sodium hydride; diisopropyl (E)-azodicarboxylate; triphenylphosphine; benzoic acid; potassium iodide; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one

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

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

(3R,4R,5S)-4-(4-hydroxy-phenyl)-5-triisopropylsilanyloxy-piperidin-3-ol

Refernces