(3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine

Base Information

• Chemical Name: (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine
• CAS No.: 277744-02-2
• Molecular Formula: C₂₄H₃₁NO₄
• Molecular Weight: 397.514
• Mol file: 277744-02-2.mol

Synonyms:(3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine

Chemical Property of (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine

There total 11 articles about (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine 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:

methyl 4-formylbutanoate (6026-86-4) → (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine (277744-02-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 13 percent / 4 Angstroem MS / toluene / 36 h / Heating

2.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

2.2: 77 percent / LiHMDS / tetrahydrofuran / 0.83 h / -78 °C

3.1: O₃; O₂ / CH₂Cl₂ / -78 - 25 °C

4.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

5.1: 86 percent / AlCl₃; LiAlH₄ / tetrahydrofuran / 3.5 h / -78 - 25 °C

6.1: 88 percent / H₂ / 20percent Pd(OH)2-C / ethyl acetate / 15 h / 25 °C

7.1: 670 mg / pyridine / 1 h / 10 °C

8.1: 261 mg / NaH / tetrahydrofuran / 3 h / Heating

With lithium aluminium tetrahydride; aluminium trichloride; 4 Angstroem MS; hydrogen; oxygen; sodium hydride; ozone; lithium hexamethyldisilazane; 20percent Pd(OH)2-C; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; ethyl acetate; toluene; 1.1: Condensation / 2.1: Substitution / 2.2: Substitution / 3.1: Elimination / 4.1: Addition / 5.1: Reduction / 6.1: Hydrogenolysis / 7.1: mesylation / 8.1: Substitution;

DOI:10.1021/jo991816p

Reference yield:

methyl 5-hydroxypentanoate (14273-92-8) → (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine (277744-02-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 82 percent / PCC; Celite; 4 Angstroem MS / CH₂Cl₂ / 1.5 h / 25 °C

2.1: 13 percent / 4 Angstroem MS / toluene / 36 h / Heating

3.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

3.2: 77 percent / LiHMDS / tetrahydrofuran / 0.83 h / -78 °C

4.1: O₃; O₂ / CH₂Cl₂ / -78 - 25 °C

5.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

6.1: 86 percent / AlCl₃; LiAlH₄ / tetrahydrofuran / 3.5 h / -78 - 25 °C

7.1: 88 percent / H₂ / 20percent Pd(OH)2-C / ethyl acetate / 15 h / 25 °C

8.1: 670 mg / pyridine / 1 h / 10 °C

9.1: 261 mg / NaH / tetrahydrofuran / 3 h / Heating

With lithium aluminium tetrahydride; aluminium trichloride; 4 Angstroem MS; Celite; hydrogen; oxygen; sodium hydride; ozone; pyridinium chlorochromate; lithium hexamethyldisilazane; 20percent Pd(OH)2-C; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; ethyl acetate; toluene; 1.1: Oxidation / 2.1: Condensation / 3.1: Substitution / 3.2: Substitution / 4.1: Elimination / 5.1: Addition / 6.1: Reduction / 7.1: Hydrogenolysis / 8.1: mesylation / 9.1: Substitution;

DOI:10.1021/jo991816p

Reference yield:

lithium phenylcyanocuprate → (3R,4S)-1-(tert-butoxycarbonyl)-3-(p-methoxyphenoxymethyl)-4-phenylpiperidine (277744-02-2)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

2: 86 percent / AlCl₃; LiAlH₄ / tetrahydrofuran / 3.5 h / -78 - 25 °C

3: 88 percent / H₂ / 20percent Pd(OH)2-C / ethyl acetate / 15 h / 25 °C

4: 670 mg / pyridine / 1 h / 10 °C

5: 261 mg / NaH / tetrahydrofuran / 3 h / Heating

With lithium aluminium tetrahydride; aluminium trichloride; hydrogen; sodium hydride; 20percent Pd(OH)2-C; In tetrahydrofuran; pyridine; diethyl ether; ethyl acetate; 1: Addition / 2: Reduction / 3: Hydrogenolysis / 4: mesylation / 5: Substitution;

DOI:10.1021/jo991816p

upstream raw materials:

methyl 4-formylbutanoate

methyl 5-hydroxypentanoate

di-tert-butyl dicarbonate

(3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine

Downstream raw materials:

femoxetine