N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide

Base Information

Chemical Name:N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide
CAS No.:69923-82-6
Molecular Formula:C₂₄H₃₀N₂O₄Si
Molecular Weight:438.599
Hs Code.:

Synonyms:N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide

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Chemical Property of N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide

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Technology Process of N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide

There total 10 articles about N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-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: 86.0%

: 79678-82-3
2-Amino-8-(tert-butyl-dimethyl-silanyloxy)-2a,3-dihydro-2H-4-oxa-8b-aza-cyclobuta[a]naphthalen-1-one

: 103-80-0
phenylacetyl chloride

: 69923-82-6
N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide

Guidance literature:: With triethylamine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1139/v81-432

Reference yield:

: 69589-23-7
di-tert-butyldimethylsilyl-2-aminoresorcinol

: 69923-82-6
N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: p-TsOH / benzene / Heating

2: CH₂Cl₂ / 1 h / -20 °C

3: 1) ozone; 2) NaBH₄ / 1) EtOH, CH₂Cl₂, -78 deg C; 2) -40 deg C --> room temp.

4: 95 percent / Et₃N / CH₂Cl₂ / 1) -78 deg C, O_.5 h; 2) room temp., 1 h

5: 95 percent / KF / 18-crown-6 / acetonitrile

6: 85 percent / Et₃N / CH₂Cl₂ / 1) 0 deg C 10 min; 2) 1 h, room temp.

7: 86 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With potassium fluoride; sodium tetrahydroborate; toluene-4-sulfonic acid; ozone; triethylamine; 18-crown-6 ether; In dichloromethane; acetonitrile; benzene;
DOI:10.1139/v81-432

Reference yield:

: 601-89-8
2-nitroresorcinol

: 69923-82-6
N-[8-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-1,2,2a,3-tetrahydro-4-oxa-8b-aza-cyclobuta[a]naphthalen-2-yl]-2-phenyl-acetamide

Guidance literature:: Multi-step reaction with 9 steps

1: hydrogen / PtO₂ / ethanol / 2068.6 Torr

2: imidazole / dimethylformamide / Ambient temperature

3: p-TsOH / benzene / Heating

4: CH₂Cl₂ / 1 h / -20 °C

5: 1) ozone; 2) NaBH₄ / 1) EtOH, CH₂Cl₂, -78 deg C; 2) -40 deg C --> room temp.

6: 95 percent / Et₃N / CH₂Cl₂ / 1) -78 deg C, O_.5 h; 2) room temp., 1 h

7: 95 percent / KF / 18-crown-6 / acetonitrile

8: 85 percent / Et₃N / CH₂Cl₂ / 1) 0 deg C 10 min; 2) 1 h, room temp.

9: 86 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; potassium fluoride; sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; ozone; triethylamine; platinum(IV) oxide; 18-crown-6 ether; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1139/v81-432