5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one

Base Information

Chemical Name:5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one
CAS No.:97012-71-0
Molecular Formula:C₃₄H₃₇NO₄
Molecular Weight:523.672
Hs Code.:

Synonyms:5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one

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Chemical Property of 5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one

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Technology Process of 5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one

There total 12 articles about 5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-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:

: 150-84-5,67650-82-2
citronellyl-acetate

: 97012-71-0
5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) SeO₂, t-BuOOH, 2.) NaBH₄ / 1.) CH₂Cl₂, 22 deg C, 2.) MeOH

2: 95 percent / imidazole / dimethylformamide / 0 °C

3: 95 percent / LiOH / methanol / 22 °C

4: 85 percent / PCC / CH₂Cl₂ / 1 h / 22 °C

5: 73 percent / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

6: 89 percent / Dibal / CH₂Cl₂ / 0.17 h / -78 °C

7: LiH, SO₃, pyridine / 2 h / 22 °C

8: LiAlH₄ / 16 h / 22 °C

9: 96 percent / n-Bu₄N(+)F(-) / tetrahydrofuran / 22 °C

10: 82 percent / PCC / CH₂Cl₂ / 1 h / 22 °C

11: 72 percent / potassium tert-butoxide / tetrahydrofuran / 4 h

12: 2.) LDA / 1.) o-dichlorobenzene, reflux, 5 min, 2.) THF, -78, 20 min

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; selenium(IV) oxide; sulfur trioxide; potassium tert-butylate; tetrabutyl ammonium fluoride; lithium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00215a053

Reference yield:

: 97012-68-5
(2E,8E,10E)-2,6-Dimethyl-dodeca-2,8,10-trienal

: 97012-71-0
5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / potassium tert-butoxide / tetrahydrofuran / 4 h

2: 2.) LDA / 1.) o-dichlorobenzene, reflux, 5 min, 2.) THF, -78, 20 min

With potassium tert-butylate; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1021/jo00215a053

Reference yield:

: (2E,8E,10E)-2,6-Dimethyl-dodeca-2,8,10-trien-1-ol

: 97012-71-0
5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / PCC / CH₂Cl₂ / 1 h / 22 °C

2: 72 percent / potassium tert-butoxide / tetrahydrofuran / 4 h

3: 2.) LDA / 1.) o-dichlorobenzene, reflux, 5 min, 2.) THF, -78, 20 min

With potassium tert-butylate; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00215a053