1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Base Information

Chemical Name:1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone
CAS No.:791821-70-0
Molecular Formula:C₁₇H₂₁NO₃
Molecular Weight:287.359
Hs Code.:

Synonyms:1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

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Chemical Property of 1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

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Technology Process of 1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

There total 6 articles about 1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone 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: 94.0%

: 791821-69-7
1-{3-benzyloxy-2-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-3,6-dihydro-2H-pyridin-1-yl}-ethanone

: 791821-70-0
1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 2h;
DOI:10.1021/jo040226a

Reference yield:

: 100-39-0
benzyl bromide

: 791821-70-0
1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / NaH / dimethylformamide / 2 h / 25 °C

2.1: NaH / 0.33 h / 0 °C

2.2: 83 percent / dimethylformamide / 1 h / 0 °C

3.1: 90 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 16 h / Heating

4.1: 94 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

With tetrabutyl ammonium fluoride; sodium hydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo040226a

Reference yield:

: 213406-16-7
(1S,4R,5R)-5-acetylamino-4-tert-butyldimethylsilyloxy-2-cyclopenten-1-ol

: 791821-70-0
1-[(2S,3R)-3-Benzyloxy-2-((R)-1-hydroxy-allyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: Burgess reagent / tetrahydrofuran / 3 h / 70 °C

1.2: 76 percent / aq. NaH₂PO₄ / tetrahydrofuran / 72 h / 25 °C

2.1: 94 percent / NaH / dimethylformamide / 2 h / 25 °C

3.1: NaH / 0.33 h / 0 °C

3.2: 83 percent / dimethylformamide / 1 h / 0 °C

4.1: 90 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 16 h / Heating

5.1: 94 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

With Burgess Reagent; tetrabutyl ammonium fluoride; sodium hydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo040226a