(1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

Base Information

Chemical Name:(1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine
CAS No.:152088-29-4
Molecular Formula:C₂₃H₂₆BrNO₆
Molecular Weight:492.367
Hs Code.:

Synonyms:(1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

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Chemical Property of (1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

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Technology Process of (1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

There total 5 articles about (1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine 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: 52.0%

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: 152088-28-3
(R)-(6-Bromo-benzo[1,3]dioxol-5-yl)-(R)-piperidin-2-yl-methanol

: 152088-29-4
(1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

Guidance literature:: With toluene-4-sulfonic acid; In toluene; Heating;
DOI:10.1016/S0040-4020(01)89913-0

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 152088-29-4
(1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LDA / 1.) hexane, THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 10 min

2: 99 percent / NaBH₄ / ethanol / 12 h / Heating

3: 99 percent / H₂ / 10percent Pd/C / ethanol / 12 h / 760 Torr

4: 99 percent / Br₂ / acetic acid / 4 h / Ambient temperature

5: 52 percent / p-TsOH / toluene / Heating

With sodium tetrahydroborate; hydrogen; bromine; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In ethanol; acetic acid; toluene;
DOI:10.1016/S0040-4020(01)89913-0

Reference yield:

: 1025961-96-9
(3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

: 152088-29-4
(1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / NaBH₄ / ethanol / 12 h / Heating

2: 99 percent / H₂ / 10percent Pd/C / ethanol / 12 h / 760 Torr

3: 99 percent / Br₂ / acetic acid / 4 h / Ambient temperature

4: 52 percent / p-TsOH / toluene / Heating

With sodium tetrahydroborate; hydrogen; bromine; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; acetic acid; toluene;
DOI:10.1016/S0040-4020(01)89913-0