(3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

Base Information

Chemical Name:(3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
CAS No.:500131-66-8
Molecular Formula:C₂₁H₂₁BrN₂O₂
Molecular Weight:413.314
Hs Code.:

Synonyms:(3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

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Chemical Property of (3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

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Technology Process of (3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

There total 3 articles about (3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile 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: 75.0%

: 54257-94-2
1-Bromo-2-chloro-methoxybenzene

: 88056-92-2
(-)-2-cyano-6-phenyloxazolopiperidine

: 500131-66-8
(3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

Guidance literature:: (-)-2-cyano-6-phenyloxazolopiperidine; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

1-Bromo-2-chloro-methoxybenzene;
DOI:10.1016/S0040-4039(03)00890-6

Reference yield:

: 95-56-7
2-hydroxybromobenzene

: 500131-66-8
(3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / NaH; NaI / 1,2-dimethoxy-ethane / 5 h / 0 °C

2: 100 percent / sulfuryl chloride / CH₂Cl₂ / 1 h / 20 °C

3: 75 percent / LDA; HMPA / tetrahydrofuran / 0.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sulfuryl dichloride; sodium hydride; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1016/S0040-4039(03)00890-6

Reference yield:

: 592508-12-8
1-bromo-2-[(methylsulfanyl)methoxy]benzene

: 500131-66-8
(3R,5S,8aR)-5-[(2-bromophenoxy)methyl]-3-phenyl-hexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / sulfuryl chloride / CH₂Cl₂ / 1 h / 20 °C

2: 75 percent / LDA; HMPA / tetrahydrofuran / 0.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sulfuryl dichloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(03)00890-6