(3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine

Base Information

Chemical Name:(3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine
CAS No.:115353-50-9
Molecular Formula:C₂₅H₂₉NO₆
Molecular Weight:439.508
Hs Code.:

Synonyms:

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Chemical Property of (3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine

Chemical Property:

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Technology Process of (3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine

There total 24 articles about (3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine 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:

: 115275-08-6
[(4S,5S)-5-Hydroxymethyl-2-((E)-propenyl)-[1,3]dioxolan-4-yl]-methanol

: 115353-50-9
(3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) NaH / 1.) DMF, THF, from 0 deg C to room temp., 1.5 h, 2.) from -20 deg C to room temp., 2 h

2: 1.) diisobutylaluminum hydride, 2.) 28percent NH₄OH / 1.) toluene, 0 deg C, 1 h, 2.) THF, MeOH, room temp., 15 d

3: aq. NaIO₄ / methanol / 2 h / 0 °C

4: ethylenediammonium diacetate / propan-2-ol / 1.) 0 deg C, 2 h, 2.) room temp., 13 h

5: dioxane; H₂O / 3.5 h

6: 4.20 g / H₂, concd HCl / 10percent Pd/C / ethanol / 5.5 h / 760 Torr / Ambient temperature

7: pyridine / 10 h / Ambient temperature

8: NaI / butan-2-one / 12 h / Heating

9: zinc dust / aq. ethanol / 1.) 60 deg C, 2 h, 2.) reflux, 0.5 h

10: 3.90 g / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / Ambient temperature

11: 90percent hydrazine hydrate / ethanol / 0.5 h / Heating

12: 254 mg / LiAlH₄ / tetrahydrofuran / 3 h / Heating

13: 340 mg / Et₃N / CH₂Cl₂ / 0.5 h / Heating

14: 1.) dicyclohexylborane, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, room temp., 2.5 h, 2.) EtOH, 50 deg C, 1 h

15: 76 percent / pyridine / 23 h / Ambient temperature

16: triphenylphosphine, diisopropyl azodicarboxylate / 2.5 h / Ambient temperature

With pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; hydrazine hydrate; ethylenediamine diacetic acid; triethylamine; triphenylphosphine; sodium iodide; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; isopropyl alcohol; butanone;
DOI:10.3987/COM-89-S70

Reference yield:

: 115275-09-7
(2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol

: 115353-50-9
(3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) diisobutylaluminum hydride, 2.) 28percent NH₄OH / 1.) toluene, 0 deg C, 1 h, 2.) THF, MeOH, room temp., 15 d

2: aq. NaIO₄ / methanol / 2 h / 0 °C

3: ethylenediammonium diacetate / propan-2-ol / 1.) 0 deg C, 2 h, 2.) room temp., 13 h

4: dioxane; H₂O / 3.5 h

5: 4.20 g / H₂, concd HCl / 10percent Pd/C / ethanol / 5.5 h / 760 Torr / Ambient temperature

6: pyridine / 10 h / Ambient temperature

7: NaI / butan-2-one / 12 h / Heating

8: zinc dust / aq. ethanol / 1.) 60 deg C, 2 h, 2.) reflux, 0.5 h

9: 3.90 g / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / Ambient temperature

10: 90percent hydrazine hydrate / ethanol / 0.5 h / Heating

11: 254 mg / LiAlH₄ / tetrahydrofuran / 3 h / Heating

12: 340 mg / Et₃N / CH₂Cl₂ / 0.5 h / Heating

13: 1.) dicyclohexylborane, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, room temp., 2.5 h, 2.) EtOH, 50 deg C, 1 h

14: 76 percent / pyridine / 23 h / Ambient temperature

15: triphenylphosphine, diisopropyl azodicarboxylate / 2.5 h / Ambient temperature

With pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; hydrazine hydrate; ethylenediamine diacetic acid; triethylamine; triphenylphosphine; sodium iodide; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; isopropyl alcohol; butanone;
DOI:10.3987/COM-89-S70

Reference yield:

: 115275-07-5
diethyl (2R,3R)-2,3-O-((E)-crotylidene)tartrate

: 115353-50-9
(3R,4S)-3-<(1R)-benzoyloxyethyl>-4-(2-benzyloxy)-1-carbomethoxypiperidine

Guidance literature:: Multi-step reaction with 17 steps

1: NaBH₄ / methanol / 3.5 h / 0 °C

2: 1.) NaH / 1.) DMF, THF, from 0 deg C to room temp., 1.5 h, 2.) from -20 deg C to room temp., 2 h

3: 1.) diisobutylaluminum hydride, 2.) 28percent NH₄OH / 1.) toluene, 0 deg C, 1 h, 2.) THF, MeOH, room temp., 15 d

4: aq. NaIO₄ / methanol / 2 h / 0 °C

5: ethylenediammonium diacetate / propan-2-ol / 1.) 0 deg C, 2 h, 2.) room temp., 13 h

6: dioxane; H₂O / 3.5 h

7: 4.20 g / H₂, concd HCl / 10percent Pd/C / ethanol / 5.5 h / 760 Torr / Ambient temperature

8: pyridine / 10 h / Ambient temperature

9: NaI / butan-2-one / 12 h / Heating

10: zinc dust / aq. ethanol / 1.) 60 deg C, 2 h, 2.) reflux, 0.5 h

11: 3.90 g / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / Ambient temperature

12: 90percent hydrazine hydrate / ethanol / 0.5 h / Heating

13: 254 mg / LiAlH₄ / tetrahydrofuran / 3 h / Heating

14: 340 mg / Et₃N / CH₂Cl₂ / 0.5 h / Heating

15: 1.) dicyclohexylborane, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, room temp., 2.5 h, 2.) EtOH, 50 deg C, 1 h

16: 76 percent / pyridine / 23 h / Ambient temperature

17: triphenylphosphine, diisopropyl azodicarboxylate / 2.5 h / Ambient temperature

With pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; hydrazine hydrate; ethylenediamine diacetic acid; triethylamine; triphenylphosphine; sodium iodide; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; isopropyl alcohol; butanone;
DOI:10.3987/COM-89-S70