(5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

Base Information

Chemical Name:(5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one
CAS No.:169304-56-7
Molecular Formula:C₁₈H₂₃NO₃
Molecular Weight:301.386
Hs Code.:

Synonyms:(5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

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Chemical Property of (5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

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Technology Process of (5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

There total 7 articles about (5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-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: 49.9%

: 100-39-0
benzyl bromide

: (5S,8aS)-5-But-3-enyl-8-hydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one

: 169304-56-7
(5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

: (5S,8S,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

Guidance literature:: With tetrabutylammomium bromide; sodium hydride; In tetrahydrofuran;
DOI:10.1016/0957-4166(95)00189-V

Reference yield:

: 169304-54-5
(S)-3-(1-Oxooct-7-en-4-yl)-2,3-dihydrooxazol-2-one

: 169304-56-7
(5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / Bu₃SnH, AIBN / benzene / 5 h / Heating

2: 49.9 percent / NaH, Bu₄NBr / tetrahydrofuran; dimethylformamide / 1.) ice-cooling, 15 min, 2.) ice-cooling, 1 h, r.t., 12 h

With 2,2'-azobis(isobutyronitrile); tetrabutylammomium bromide; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19960000793

Reference yield:

: 169304-50-1
(R)-1-(tert-butyldiphenylsilyloxy)-7-octen-4-ol

: 169304-56-7
(5S,8R,8aS)-8-Benzyloxy-5-but-3-enyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

Guidance literature:: Multi-step reaction with 7 steps

1: 74.1 percent / diisopropyl azodicarboxylate, Ph₃P / tetrahydrofuran / 12 h / Ambient temperature

2: NaBH₄ / methanol / 1.) ice-cooling, 0.5 h, 2.) r.t., 2 h

3: CH₃SO₂Cl, Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

4: 97.2 percent / Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

5: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 1 h; r.t., 1 h

6: 83 percent / Bu₃SnH, AIBN / benzene / 5 h / Heating

7: 49.9 percent / NaH, Bu₄NBr / tetrahydrofuran; dimethylformamide / 1.) ice-cooling, 15 min, 2.) ice-cooling, 1 h, r.t., 12 h

With sodium tetrahydroborate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1039/P19960000793