tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate
• CAS No.: 176966-99-7
• Molecular Formula: C₁₆H₂₂FNO₃
• Molecular Weight: 295.354
• Mol file: 176966-99-7.mol

Synonyms:

Chemical Property of tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate

There total 8 articles about tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate 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:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate (176966-99-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) 1,4-diazabicyclo<2.2.2>octane, n-butyl lithium / 1.) THF, hexane, -78 deg C, 45 min, 2.) THF, hexane, -78 deg C, 2 h

2: 1.) LiHMDS / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2h

3: 30percent hydrogen peroxide / ethyl acetate / 0.75 h / Ambient temperature

4: 1.) CuBr*SMe₂, 2.) TMSCl / 1.) Et₂O, -40 deg C, 30 min, 2.) Et₂O, -70 deg C, 2 h

5: 1.) lithium triethylborohydride, 2.) triethylsilane, boron trifluoride etherate / 1.) CH₂Cl₂, THF, -78 deg C, 30 min, 2.) CH₂Cl₂, -78 deg C, 2 h

6: 74 percent / n-Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; triethylsilane; n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium triethylborohydride; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/0957-4166(96)00085-7

Reference yield:

(S)-5-hydroxypiperidin-2-one (24211-54-9) → tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate (176966-99-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 1.) 1,4-diazabicyclo<2.2.2>octane, n-butyl lithium / 1.) THF, hexane, -78 deg C, 45 min, 2.) THF, hexane, -78 deg C, 2 h

3: 1.) LiHMDS / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2h

4: 30percent hydrogen peroxide / ethyl acetate / 0.75 h / Ambient temperature

5: 1.) CuBr*SMe₂, 2.) TMSCl / 1.) Et₂O, -40 deg C, 30 min, 2.) Et₂O, -70 deg C, 2 h

6: 1.) lithium triethylborohydride, 2.) triethylsilane, boron trifluoride etherate / 1.) CH₂Cl₂, THF, -78 deg C, 30 min, 2.) CH₂Cl₂, -78 deg C, 2 h

7: 74 percent / n-Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; triethylsilane; n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium triethylborohydride; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0957-4166(96)00085-7

Reference yield:

4-flourophenylmagnesium bromide (352-13-6) → tert-butyl (3S,4S)-4-(4'-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate (176966-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) CuBr*SMe₂, 2.) TMSCl / 1.) Et₂O, -40 deg C, 30 min, 2.) Et₂O, -70 deg C, 2 h

2: 1.) lithium triethylborohydride, 2.) triethylsilane, boron trifluoride etherate / 1.) CH₂Cl₂, THF, -78 deg C, 30 min, 2.) CH₂Cl₂, -78 deg C, 2 h

3: 74 percent / n-Bu₄NF / tetrahydrofuran / 18 h / Ambient temperature

With triethylsilane; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1016/0957-4166(96)00085-7

upstream raw materials:

di-tert-butyl dicarbonate

(S)-5-hydroxypiperidin-2-one

4-flourophenylmagnesium bromide

(5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one

Refernces