N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide

Base Information

Chemical Name:N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide
CAS No.:118378-07-7
Molecular Formula:C₃₃H₃₉NO₄
Molecular Weight:513.677
Hs Code.:

Synonyms:N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide

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Chemical Property of N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide

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Technology Process of N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide

There total 19 articles about N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide 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: 60.0%

: 93-97-0
benzoic acid anhydride

: 124665-34-5
(1S,2aS,3S,4aR,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,5,6,8b-octahydro-4aH-cyclobuta[a]naphthalen-7-one oxime

: 118378-07-7
N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide

Guidance literature:: In xylene; Heating;
DOI:10.1021/jo00261a046

Reference yield:

: 118378-03-3
(1S,5S,6R,8S)-5-Benzyloxymethyl-8-(1-hydroxy-1-methyl-ethyl)-bicyclo[4.2.0]octan-2-one

: 118378-07-7
N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: i-Pr₂NEt / CH₂Cl₂ / 70 h / 20 °C

2.1: sodium hydride / tetrahydrofuran / 3 h / 20 °C

2.2: aq. HCl / tetrahydrofuran / pH 5

3.1: Et₃N / tetrahydrofuran / 7 h / 0 - 20 °C

4.1: aq. potassium hydroxide / methanol / Heating

5.1: 83 percent / hydroxylamine hydrochloride; sodium acetate / methanol / 3 h / Heating

6.1: xylene / 4.5 h / 110 °C

With potassium hydroxide; hydroxylamine hydrochloride; sodium acetate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; xylene; 6.1: Semmler-Wolff aniline aromatization;
DOI:10.1021/ja034842k

Reference yield:

: 573699-09-9
(1S,5S,6R,8S)-5-Benzyloxymethyl-8-(1-methoxymethoxy-1-methyl-ethyl)-bicyclo[4.2.0]octan-2-one

: 118378-07-7
N-[(1S,2aS,3S,8bS)-3-Benzyloxymethyl-1-(1-methoxymethoxy-1-methyl-ethyl)-8-methyl-1,2,2a,3,4,8b-hexahydro-cyclobuta[a]naphthalen-7-yl]-benzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 3 h / 20 °C

1.2: aq. HCl / tetrahydrofuran / pH 5

2.1: Et₃N / tetrahydrofuran / 7 h / 0 - 20 °C

3.1: aq. potassium hydroxide / methanol / Heating

4.1: 83 percent / hydroxylamine hydrochloride; sodium acetate / methanol / 3 h / Heating

5.1: xylene / 4.5 h / 110 °C

With potassium hydroxide; hydroxylamine hydrochloride; sodium acetate; sodium hydride; triethylamine; In tetrahydrofuran; methanol; xylene; 5.1: Semmler-Wolff aniline aromatization;
DOI:10.1021/ja034842k