(3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 108943-51-7
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• Mol file: 108943-51-7.mol

Synonyms:(3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Chemical Property of (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

There total 23 articles about (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester 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:

3-(2-azidoethyl)-3-deoxy-1,2:5,6-di-O-isopropylideneallofuranose → (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (108943-51-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / acetic acid, H₂O / methanol / 40 °C

2: 1.) NaIO₄, 2.) H₂ / 2.) palladium black / 1.) MeOH, H₂O, 2.) AcOH

3: NaHCO₃ / diethyl ether; H₂O / 20 °C

4: 52 percent / Dowex H⁽¹⁺⁾ resin

5: NaH / tetrahydrofuran / 20 °C

6: 87 percent / tributyltin hydride, AIBN / xylene / 110 °C

7: aqueous trifluoroacetic acid / 20 °C

8: sodium borohydride / ethanol; H₂O

With sodium tetrahydroborate; sodium periodate; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; acetic acid; trifluoroacetic acid; Dowex H⁽¹⁺⁾ resin; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; xylene;

DOI:10.1016/S0040-4039(00)84715-2

Reference yield:

[(3aR,5S,6aR)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-acetic acid methyl ester (18427-16-2,18427-17-3,40005-22-9,43169-39-7,43169-40-0,58845-96-8,58846-03-0) → (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (108943-51-7)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂ / Pd / methanol

2: LiAlH₄ / tetrahydrofuran

3: pyridine / 0 °C

4: NaN₃ / dimethylformamide / 40 °C

5: 90 percent / acetic acid, H₂O / methanol / 40 °C

6: 1.) NaIO₄, 2.) H₂ / 2.) palladium black / 1.) MeOH, H₂O, 2.) AcOH

7: NaHCO₃ / diethyl ether; H₂O / 20 °C

8: 52 percent / Dowex H⁽¹⁺⁾ resin

9: NaH / tetrahydrofuran / 20 °C

10: 87 percent / tributyltin hydride, AIBN / xylene / 110 °C

11: aqueous trifluoroacetic acid / 20 °C

12: sodium borohydride / ethanol; H₂O

With pyridine; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; sodium azide; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; acetic acid; trifluoroacetic acid; Dowex H⁽¹⁺⁾ resin; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)84715-2

Reference yield:

Methanesulfonic acid 2-[(3aR,5S,6R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-ethyl ester → (3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (108943-51-7)

Guidance literature:

Multi-step reaction with 9 steps

1: NaN₃ / dimethylformamide / 40 °C

2: 90 percent / acetic acid, H₂O / methanol / 40 °C

3: 1.) NaIO₄, 2.) H₂ / 2.) palladium black / 1.) MeOH, H₂O, 2.) AcOH

4: NaHCO₃ / diethyl ether; H₂O / 20 °C

5: 52 percent / Dowex H⁽¹⁺⁾ resin

6: NaH / tetrahydrofuran / 20 °C

7: 87 percent / tributyltin hydride, AIBN / xylene / 110 °C

8: aqueous trifluoroacetic acid / 20 °C

9: sodium borohydride / ethanol; H₂O

With sodium tetrahydroborate; sodium periodate; sodium azide; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; acetic acid; trifluoroacetic acid; Dowex H⁽¹⁺⁾ resin; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)84715-2

upstream raw materials:

(4aR,8aS)-4,4a,5,6,8,8a-Hexahydro-pyrano[2,3-c]pyridine-7-carboxylic acid benzyl ester

Methyl 4-C-<(Dimethylcarboxamido)methyl>-2,3,4-trideoxy-α-D-erythrohex-2-enopyranoside

(2S,4aR,8aS)-2-Methoxy-hexahydro-pyrano[2,3-c]pyridin-6-one

(2S,4aR,8aS)-2-Methoxy-octahydro-pyrano[2,3-c]pyridine-7-carboxylic acid benzyl ester

Downstream raw materials:

(3S,4S)-3-Hydroxy-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

(3aS,7aS)-Hexahydro-furo[2,3-c]pyridine-6-carboxylic acid benzyl ester

(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

(S)-3-quinuclidinol