(3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 188874-42-2
• Molecular Formula: C₂₆H₃₅NO₆
• Molecular Weight: 457.567

Synonyms:(3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of (3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester

There total 10 articles about (3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl 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: 89.0%

1-[(3-bromopropoxy)methyl]-benzene (54314-84-0) + (3R,4S,5S)-3,5-Dihydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (188874-91-1) → (3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester (188874-42-2)

Guidance literature:

With potassium carbonate; In butanone; Heating;

DOI:10.1016/S0960-894X(99)00196-1

Reference yield:

1-benzyl-4-(4-methoxy-phenyl)-1,2,3,6-tetrahydro-pyridine (13314-69-7) → (3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester (188874-42-2)

Guidance literature:

Multi-step reaction with 10 steps

1: aq. HBr / toluene / Ambient temperature

2: NaBr, Br₂ / H₂O; dioxane

3: aq. NaOH / dioxane / 0 - 20 °C

4: BuLi / tetrahydrofuran / Heating

5: NaH / tetrahydrofuran / 20 - 35 °C

6: 1.) NaBH₄, BF₃*Et₂O, 2.) aq. KOH, 3.) 30 percent aq. H₂O₂

7: 91 percent / BBr₃ / CH₂Cl₂ / 40 °C

8: 97 percent / H₂ / Pd/C / methanol / Ambient temperature

9: 91 percent / NaHCO₃ / H₂O; dioxane / Ambient temperature

10: 89 percent / K₂CO₃ / butan-2-one / Heating

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; hydrogen bromide; hydrogen; dihydrogen peroxide; bromine; boron tribromide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; butanone;

DOI:10.1016/S0960-894X(99)00196-1

Reference yield:

1-benzyl-4-bromo-4-(4-methoxy-phenyl)-piperidine → (3R,4S,5S)-4-[4-(3-Benzyloxy-propoxy)-phenyl]-3,5-dihydroxy-piperidine-1-carboxylic acid tert-butyl ester (188874-42-2)

Guidance literature:

Multi-step reaction with 9 steps

1: NaBr, Br₂ / H₂O; dioxane

2: aq. NaOH / dioxane / 0 - 20 °C

3: BuLi / tetrahydrofuran / Heating

4: NaH / tetrahydrofuran / 20 - 35 °C

5: 1.) NaBH₄, BF₃*Et₂O, 2.) aq. KOH, 3.) 30 percent aq. H₂O₂

6: 91 percent / BBr₃ / CH₂Cl₂ / 40 °C

7: 97 percent / H₂ / Pd/C / methanol / Ambient temperature

8: 91 percent / NaHCO₃ / H₂O; dioxane / Ambient temperature

9: 89 percent / K₂CO₃ / butan-2-one / Heating

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; bromine; boron tribromide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; butanone;

DOI:10.1016/S0960-894X(99)00196-1

upstream raw materials:

1-[(3-bromopropoxy)methyl]-benzene

(3R,4S,5S)-3,5-Dihydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

1-benzyl-4-(4-methoxy-phenyl)-1,2,3,6-tetrahydro-pyridine

(3R,4S,5S)-4-(4-Hydroxy-phenyl)-piperidine-3,5-diol

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