(-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

Base Information

Chemical Name:(-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide
CAS No.:865769-22-8
Molecular Formula:C₁₈H₂₃NO₂
Molecular Weight:285.386
Hs Code.:

Synonyms:(-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

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Chemical Property of (-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

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Technology Process of (-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

There total 5 articles about (-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide 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: 80.0%

: myrtenic acid chloride

: 20989-17-7
(2S)-2-phenylglycinol

: 865769-22-8
(-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

Guidance literature:: With triethylamine; In 1,4-dioxane; at 10 ℃;
DOI:10.1002/ejoc.200500144

Reference yield:

: 564-94-3,18486-69-6
myrtenal

: 865769-22-8
(-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1: NH₂OH*HCl; NaHCO₃ / ethanol; H₂O / 20 h / Heating

2: 67.9 g / Ac₂O; NaOAc / 120 h / 100 °C

3: 99 percent / aq. NaOH; aq. H₂O₂ / 96 h / Heating

4: (COCl)2; DMF / toluene / 20 °C

5: 80 percent / Et₃N / dioxane / 10 °C

With sodium hydroxide; oxalyl dichloride; hydroxylamine hydrochloride; dihydrogen peroxide; sodium acetate; acetic anhydride; sodium hydrogencarbonate; triethylamine; N,N-dimethyl-formamide; In 1,4-dioxane; ethanol; water; toluene;
DOI:10.1002/ejoc.200500144

Reference yield:

: 92834-76-9
(-)-(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbonitrile

: 865769-22-8
(-)-(1R,5S)-N-[2-hydroxy-(1S)-phenylethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / aq. NaOH; aq. H₂O₂ / 96 h / Heating

2: (COCl)2; DMF / toluene / 20 °C

3: 80 percent / Et₃N / dioxane / 10 °C

With sodium hydroxide; oxalyl dichloride; dihydrogen peroxide; triethylamine; N,N-dimethyl-formamide; In 1,4-dioxane; toluene;
DOI:10.1002/ejoc.200500144