(3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol

Base Information

Chemical Name:(3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol
CAS No.:277743-97-2
Molecular Formula:C₁₇H₂₅NO₃
Molecular Weight:291.39
Hs Code.:

Synonyms:(3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol

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Chemical Property of (3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol

Chemical Property:

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Technology Process of (3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol

There total 14 articles about (3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-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: 100.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 872544-55-3
rel-[(3R,4S)-4-phenylpiperidin-3-yl]methanol

: 277743-97-2
(3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol

Guidance literature:: With sodium carbonate; In dichloromethane; water; at 0 ℃; for 1h;
DOI:10.1016/j.tetlet.2005.10.049

Reference yield:

: 6026-86-4
methyl 4-formylbutanoate

: 277743-97-2
(3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol

Guidance literature:: Multi-step reaction with 6 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

With lithium aluminium tetrahydride; aluminium trichloride; 4 Angstroem MS; hydrogen; oxygen; ozone; lithium hexamethyldisilazane; 20percent Pd(OH)2-C; In tetrahydrofuran; 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;
DOI:10.1021/jo991816p

Reference yield:

: 14273-92-8
methyl 5-hydroxypentanoate

: 277743-97-2
(3R,4S)-1-(tert-butoxycarbonyl)-4-phenyl-3-piperidinemethanol

Guidance literature:: Multi-step reaction with 7 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

With lithium aluminium tetrahydride; aluminium trichloride; 4 Angstroem MS; Celite; hydrogen; oxygen; ozone; pyridinium chlorochromate; lithium hexamethyldisilazane; 20percent Pd(OH)2-C; In tetrahydrofuran; 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;
DOI:10.1021/jo991816p