3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

Base Information

Chemical Name:3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one
CAS No.:79632-07-8
Molecular Formula:C₁₈H₂₃NO₃
Molecular Weight:301.386
Hs Code.:

Synonyms:3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

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Chemical Property of 3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

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Technology Process of 3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

There total 7 articles about 3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-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: 80.0%

: 79632-06-7
2,3β-dibenzyl-5α,6-dimethyl-8α-<(benzyloxy)methyl>-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

: 79632-07-8
3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

Guidance literature:: With ammonia; lithium; In tetrahydrofuran;
DOI:10.1021/jo00339a027

Reference yield:

: 70849-69-3,30338-90-0,57258-51-2
(2E,4E)-4-methylhexa-2,4-dien-1-ol

: 79632-07-8
3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) dimethoxyethane, room temperature, 2 h, 2.) room temperature, overnight

2: 83 percent / toluene / 5 h / Heating

3: 64 percent / diisobutylaluminum hydride / toluene; hexane / 0.25 h / -78 °C

4: 93 percent / dilute HCl / 0.5 h / 0 °C

5: 1.) AlCl₃ / 1.) ether, THF, a) room temperature, overnight, b) reflux, 3 h, 2.) toluene, reflux, 2.5 h

6: 1.) n-BuLi, hexamethyldisilazane, 2.) O₂, P(OMe)3 / 1.) THF, hexane, 0 deg C, 1 h, 2.) room temperature, 2 h

7: 80 percent / Li, liq. NH₃ / tetrahydrofuran

With hydrogenchloride; n-butyllithium; aluminium trichloride; ammonia; oxygen; lithium; sodium hydride; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; phosphorous acid trimethyl ester; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo00339a027

Reference yield:

: 86544-85-6
3-methyl-6-(benzyloxy)-2,4-hexadiene

: 79632-07-8
3β-benzyl-5α,6-dimethyl-8α-(hydroxymethyl)-9β-hydroxy-2,3α,4β,5β,8β,9-hexahydro-1H-isoindol-1-one

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / toluene / 5 h / Heating

2: 64 percent / diisobutylaluminum hydride / toluene; hexane / 0.25 h / -78 °C

3: 93 percent / dilute HCl / 0.5 h / 0 °C

4: 1.) AlCl₃ / 1.) ether, THF, a) room temperature, overnight, b) reflux, 3 h, 2.) toluene, reflux, 2.5 h

5: 1.) n-BuLi, hexamethyldisilazane, 2.) O₂, P(OMe)3 / 1.) THF, hexane, 0 deg C, 1 h, 2.) room temperature, 2 h

6: 80 percent / Li, liq. NH₃ / tetrahydrofuran

With hydrogenchloride; n-butyllithium; aluminium trichloride; ammonia; oxygen; lithium; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; phosphorous acid trimethyl ester; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo00339a027