4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid

Base Information

• Chemical Name: 4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid
• CAS No.: 1394132-11-6
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48
• Mol file: 1394132-11-6.mol

Synonyms:4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid

Chemical Property of 4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid

There total 13 articles about 4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid 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: 95.0%

(2S,4S,5R)-tert-butyl-2-(3-cyanopropyl)-4-hydroxy-5-(4-methoxyphenyl)piperidine-1-carboxylate (1394132-05-8) → 4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid (1394132-11-6)

Guidance literature:

(2S,4S,5R)-tert-butyl-2-(3-cyanopropyl)-4-hydroxy-5-(4-methoxyphenyl)piperidine-1-carboxylate; With sodium hydroxide; In ethanol; water; at 85 ℃; for 16h; Inert atmosphere;

With hydrogenchloride; In water; pH=4; Inert atmosphere;

DOI:10.1039/c2ob25689d

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid (1394132-11-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: N¹,N¹-dimethyl-N²-(((S)-pyrrolidin-2-yl)methyl)ethane-1,2-diamine; toluene-4-sulfonic acid / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

2.1: disodium phosphate heptahydrate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / ethanol / 3 h / 20 °C / Inert atmosphere

4.1: collidine / dichloromethane / 4 h / -78 °C / Inert atmosphere

5.1: iodine / acetone / 1 h / 20 °C / Inert atmosphere

6.1: ammonium chloride; zinc / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

7.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 1 h / 0 °C / Inert atmosphere

8.1: titanium(III) chloride / methanol; water / 4 h / 0 °C / Inert atmosphere

8.2: Inert atmosphere

9.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.25 h / 0 °C / Inert atmosphere

11.1: dimethyl sulfoxide / 2 h / 20 - 70 °C / Inert atmosphere

12.1: sodium hydroxide / ethanol; water / 16 h / 85 °C / Inert atmosphere

12.2: pH 4 / Inert atmosphere

With N¹,N¹-dimethyl-N²-(((S)-pyrrolidin-2-yl)methyl)ethane-1,2-diamine; sodium tetrahydroborate; titanium(III) chloride; disodium phosphate heptahydrate; iodine; ammonium chloride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; tetramethylammonium triacetoxyborohydride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: Michael condensation / 2.1: Baeyer-Villiger oxidation;

DOI:10.1039/c2ob25689d

Reference yield:

3-(2-((2S,3R)-2-hydroxy-3-(4-methoxyphenyl)-4-nitrobutyl)-1,3-dioxolan-2-yl)propyl acetate (1394131-95-3) → 4-((2S,4S,5R)-1-(tert-butoxycarbonyl)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoic acid (1394132-11-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: iodine / acetone / 1 h / 20 °C / Inert atmosphere

2.1: ammonium chloride; zinc / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

3.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 1 h / 0 °C / Inert atmosphere

4.1: titanium(III) chloride / methanol; water / 4 h / 0 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.25 h / 0 °C / Inert atmosphere

7.1: dimethyl sulfoxide / 2 h / 20 - 70 °C / Inert atmosphere

8.1: sodium hydroxide / ethanol; water / 16 h / 85 °C / Inert atmosphere

8.2: pH 4 / Inert atmosphere

With titanium(III) chloride; iodine; ammonium chloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; tetramethylammonium triacetoxyborohydride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile;

DOI:10.1039/c2ob25689d

upstream raw materials:

cyclohexanedione monoethylene ketal

(7S)-7-[(1R)-1-(4-methoxyphenyl)-2-nitroethyl]-1,4-dioxaspiro[4.5]decan-8-one

(S)-7-((R)-1-(4-methoxyphenyl)-2-nitroethyl)-1,4,8-trioxaspiro[4.6]undecan-9-one

(2S,4S,5R)-2-(3-hydroxypropyl)-5-(4-methoxyphenyl)piperidin-4-ol

Downstream raw materials:

methyl 4-((2S,4S,5R)-4-hydroxy-5-(4-methoxyphenyl)piperidin-2-yl)butanoate