(3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol

Base Information

Chemical Name:(3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol
CAS No.:277743-96-1
Molecular Formula:C₂₀H₂₄FNO₂
Molecular Weight:329.414
Hs Code.:

Synonyms:(3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol

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Chemical Property of (3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol

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Technology Process of (3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol

There total 8 articles about (3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol 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: 74.0%

: 277743-73-4
(3R,6R,7S,8aS)-7-(p-fluorophenyl)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 277743-96-1
(3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol

Guidance literature:: With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; at -78 - 25 ℃; for 3.5h;
DOI:10.1021/jo991816p

Reference yield:

: 6026-86-4
methyl 4-formylbutanoate

: 277743-96-1
(3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol

Guidance literature:: Multi-step reaction with 5 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: 74 percent / AlCl₃; LiAlH₄ / tetrahydrofuran / 3.5 h / -78 - 25 °C

With lithium aluminium tetrahydride; aluminium trichloride; 4 Angstroem MS; oxygen; ozone; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Condensation / 2.1: Substitution / 2.2: Substitution / 3.1: Elimination / 4.1: Addition / 5.1: Reduction;
DOI:10.1021/jo991816p

Reference yield:

: 14273-92-8
methyl 5-hydroxypentanoate

: 277743-96-1
(3R,4S)-4-(p-fluorophenyl)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-piperidinemethanol

Guidance literature:: Multi-step reaction with 6 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: 74 percent / AlCl₃; LiAlH₄ / tetrahydrofuran / 3.5 h / -78 - 25 °C

With lithium aluminium tetrahydride; aluminium trichloride; 4 Angstroem MS; Celite; oxygen; ozone; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Oxidation / 2.1: Condensation / 3.1: Substitution / 3.2: Substitution / 4.1: Elimination / 5.1: Addition / 6.1: Reduction;
DOI:10.1021/jo991816p