(3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

Base Information

Chemical Name:(3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one
CAS No.:727975-20-4
Molecular Formula:C₂₂H₂₅NO₃
Molecular Weight:351.445
Hs Code.:

Synonyms:(3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

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Chemical Property of (3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

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Technology Process of (3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

There total 1 articles about (3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 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: 38.0%

: 100-39-0
benzyl bromide

: (3R,8R,8aS)-8a-Methyl-5-oxo-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-8-carboxylic acid methyl ester

: 727975-20-4
(3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

: 727975-23-7
(3R,8R,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

Guidance literature:: (3R,8R,8aS)-8a-Methyl-5-oxo-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-8-carboxylic acid methyl ester; With lithium aluminium tetrahydride; 8aS-Me-5-oxo-3R-Ph-hexahydro-oxazolo[3,2-a]pyridine-8S-COOMe; In tetrahydrofuran; at 0 - 20 ℃; for 5h;

benzyl bromide; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 24h; Further stages.;
DOI:10.1016/j.tetlet.2004.04.121

Reference yield: 44.0%

: 727975-20-4
(3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

: 727975-21-5
(3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-2,3,8,8a-tetrahydro-oxazolo[3,2-a]pyridin-5-one

Guidance literature:: (3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one; With Phenylselenyl bromide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 1.5h; Further stages.;
DOI:10.1016/j.tetlet.2004.04.121

Reference yield:

: 727975-20-4
(3R,8S,8aS)-8-Benzyloxymethyl-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

: 727975-26-0
(3R,4S,5R,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiHMDS; PhSeBr / tetrahydrofuran / -78 °C

1.2: 44 percent / mCPBA / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 51 percent / OsO₄; Ba(ClO₃)2 / tetrahydrofuran; H₂O / 96 h

3.1: 34 percent / BH₃*DMS / tetrahydrofuran / 24 h / 0 - 20 °C

With osmium(VIII) oxide; barium chlorate; dimethylsulfide borane complex; Phenylselenyl bromide; lithium hexamethyldisilazane; In tetrahydrofuran; water;
DOI:10.1016/j.tetlet.2004.04.121