2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide

Base Information

Chemical Name:2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide
CAS No.:438627-84-0
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

Synonyms:

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Chemical Property of 2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide

Chemical Property:

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Technology Process of 2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide

There total 12 articles about 2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide 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:

: 2859-78-1
4-Bromoveratrole

: 438627-84-0
2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide

Guidance literature:: Multi-step reaction with 11 steps

1: 80 percent / butyllithium / tetrahydrofuran / -78 °C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

3: pyridinium chlorochromate; NaOAc

4: acetic acid / 40 °C

5: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

6: 76 percent / decahydronaphthalene / 220 °C

7: H₂ / Pd-C / ethyl acetate

8: p-TsOH / methanol / Heating

9: 88 percent / Dess-Martin periodinane / CH₂Cl₂

10: CeCl₃ / tetrahydrofuran / -20 °C

11: Me₃Al / tetrahydrofuran / Heating

With sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium acetate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; decalin; 6: Eschenmoser reaction;
DOI:10.1016/S0040-4039(02)00033-3

Reference yield:

: 288269-05-6
(3aS,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

: 438627-84-0
2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide

Guidance literature:: Multi-step reaction with 11 steps

1: 80 percent / butyllithium / tetrahydrofuran / -78 °C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

3: pyridinium chlorochromate; NaOAc

4: acetic acid / 40 °C

5: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

6: 76 percent / decahydronaphthalene / 220 °C

7: H₂ / Pd-C / ethyl acetate

8: p-TsOH / methanol / Heating

9: 88 percent / Dess-Martin periodinane / CH₂Cl₂

10: CeCl₃ / tetrahydrofuran / -20 °C

11: Me₃Al / tetrahydrofuran / Heating

With sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium acetate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; decalin; 6: Eschenmoser reaction;
DOI:10.1016/S0040-4039(02)00033-3

Reference yield:

: 438627-76-0
(3aR,6aR)-6-(3,4-Dimethoxy-phenyl)-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 438627-84-0
2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2,3-dihydroxy-3-methyl-cyclopentyl]-N-methyl-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -20 °C

2: 76 percent / decahydronaphthalene / 220 °C

3: H₂ / Pd-C / ethyl acetate

4: p-TsOH / methanol / Heating

5: 88 percent / Dess-Martin periodinane / CH₂Cl₂

6: CeCl₃ / tetrahydrofuran / -20 °C

7: Me₃Al / tetrahydrofuran / Heating

With sodium tetrahydroborate; cerium(III) chloride; hydrogen; trimethylaluminum; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; decalin; 2: Eschenmoser reaction;
DOI:10.1016/S0040-4039(02)00033-3