(1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-8-one

Base Information

• Chemical Name: (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-8-one
• CAS No.: 178681-82-8
• Molecular Formula: C₁₅H₁₇NO₃
• Molecular Weight: 259.305

Synonyms:

Chemical Property of (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-8-one

There total 19 articles about (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-8-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:

ETHYL 3-METHOXYPHENYLACETATE (35553-92-5) → (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-8-one (178681-82-8)

Guidance literature:

Multi-step reaction with 19 steps

1: 72 percent / NaH / benzene; paraffin / 2.5 h / Heating

2: 90 percent / 1.) NaH / paraffin; 1,2-dimethoxy-ethane / 18 h / Ambient temperature; 1.) room temp., 40 min

3: 70 percent / PLE, pH 8.04 phosphate buffer / acetone / 10 h / Ambient temperature

4: 96 percent / LiBH₄ / tetrahydrofuran / 1 h / 55 °C

5: 78 percent / sulfuric acid / benzene / 45 h / Heating

6: PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

7: 1.) NaH / tetrahydrofuran; paraffin / 14 h / Ambient temperature; 1.) THF, mineral oil, room temp., 40 min

8: 97 percent / hydrogen / 5percent Pd/C / methanol / 20 h

9: NaOH / ethanol / 1 h / Heating

10: 56 percent / PPA / 1 h / 100 °C

11: hydrogen, 10percent HCl / PtO₂ / ethanol / 4 h

12: 89 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

13: 90 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

14: 89 percent / NH₂OH*HCl, AcONa / ethanol / 40 h / Ambient temperature

15: hydrogen / PtO₂ / acetic acid / 17 h / Ambient temperature

16: 93 percent / acetic acid / 4 h / Heating

17: 52 percent / K₂Cr₂O₇, 10N H₂SO₄ / acetic acid; H₂O / 15 h / Ambient temperature

18: Br₂ / benzene; tetrahydrofuran / 2 h / Ambient temperature

19: NaOMe / methanol / 5 h / Heating

With hydrogenchloride; potassium dichromate; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; Celite; pH 8.04 phosphate buffer; sulfuric acid; hydroxylamine hydrochloride; hydrogen; bromine; sodium methylate; sodium acetate; sodium hydride; pyridinium chlorochromate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetic acid; acetone; paraffin; benzene;

DOI:10.3987/COM-96-7421

Reference yield:

2-(3-methoxyphenyl)malonic acid diethyl ester (50874-07-2) → (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-8-one (178681-82-8)

Guidance literature:

Multi-step reaction with 18 steps

1: 90 percent / 1.) NaH / paraffin; 1,2-dimethoxy-ethane / 18 h / Ambient temperature; 1.) room temp., 40 min

2: 70 percent / PLE, pH 8.04 phosphate buffer / acetone / 10 h / Ambient temperature

3: 96 percent / LiBH₄ / tetrahydrofuran / 1 h / 55 °C

4: 78 percent / sulfuric acid / benzene / 45 h / Heating

5: PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

6: 1.) NaH / tetrahydrofuran; paraffin / 14 h / Ambient temperature; 1.) THF, mineral oil, room temp., 40 min

7: 97 percent / hydrogen / 5percent Pd/C / methanol / 20 h

8: NaOH / ethanol / 1 h / Heating

9: 56 percent / PPA / 1 h / 100 °C

10: hydrogen, 10percent HCl / PtO₂ / ethanol / 4 h

11: 89 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

12: 90 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

13: 89 percent / NH₂OH*HCl, AcONa / ethanol / 40 h / Ambient temperature

14: hydrogen / PtO₂ / acetic acid / 17 h / Ambient temperature

15: 93 percent / acetic acid / 4 h / Heating

16: 52 percent / K₂Cr₂O₇, 10N H₂SO₄ / acetic acid; H₂O / 15 h / Ambient temperature

17: Br₂ / benzene; tetrahydrofuran / 2 h / Ambient temperature

18: NaOMe / methanol / 5 h / Heating

With hydrogenchloride; potassium dichromate; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; Celite; pH 8.04 phosphate buffer; sulfuric acid; hydroxylamine hydrochloride; hydrogen; bromine; sodium methylate; sodium acetate; sodium hydride; pyridinium chlorochromate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetic acid; acetone; paraffin; benzene;

DOI:10.3987/COM-96-7421

Reference yield:

diethyl (3-methoxyphenyl)methylpropanedioate (83026-48-6) → (1R,9S)-10-Acetyl-4-methoxy-1-methyl-10-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-8-one (178681-82-8)

Guidance literature:

Multi-step reaction with 17 steps

1: 70 percent / PLE, pH 8.04 phosphate buffer / acetone / 10 h / Ambient temperature

2: 96 percent / LiBH₄ / tetrahydrofuran / 1 h / 55 °C

3: 78 percent / sulfuric acid / benzene / 45 h / Heating

4: PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

5: 1.) NaH / tetrahydrofuran; paraffin / 14 h / Ambient temperature; 1.) THF, mineral oil, room temp., 40 min

6: 97 percent / hydrogen / 5percent Pd/C / methanol / 20 h

7: NaOH / ethanol / 1 h / Heating

8: 56 percent / PPA / 1 h / 100 °C

9: hydrogen, 10percent HCl / PtO₂ / ethanol / 4 h

10: 89 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

11: 90 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

12: 89 percent / NH₂OH*HCl, AcONa / ethanol / 40 h / Ambient temperature

13: hydrogen / PtO₂ / acetic acid / 17 h / Ambient temperature

14: 93 percent / acetic acid / 4 h / Heating

15: 52 percent / K₂Cr₂O₇, 10N H₂SO₄ / acetic acid; H₂O / 15 h / Ambient temperature

16: Br₂ / benzene; tetrahydrofuran / 2 h / Ambient temperature

17: NaOMe / methanol / 5 h / Heating

With hydrogenchloride; potassium dichromate; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; Celite; pH 8.04 phosphate buffer; sulfuric acid; hydroxylamine hydrochloride; hydrogen; bromine; sodium methylate; sodium acetate; sodium hydride; pyridinium chlorochromate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; acetone; paraffin; benzene;

DOI:10.3987/COM-96-7421

upstream raw materials:

ETHYL 3-METHOXYPHENYLACETATE

2-(3-methoxyphenyl)malonic acid diethyl ester

diethyl (3-methoxyphenyl)methylpropanedioate

(R)-1,2,3,4-tetrahydro-7-methoxy-1-methyl-1-naphthalenemethanol

Downstream raw materials:

(-)-aphanorphine

(+)-8-O-methylaphanorphine

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