9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.0^1,5]dodecane-2,12-dione

Base Information

• Chemical Name: 9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.0^1,5]dodecane-2,12-dione
• CAS No.: 98689-10-2
• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.368

Synonyms:9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.0^1,5]dodecane-2,12-dione

Chemical Property of 9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.0^1,5]dodecane-2,12-dione

Chemical Property:

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Technology Process of 9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.0^1,5]dodecane-2,12-dione

There total 10 articles about 9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.0^1,5]dodecane-2,12-dione 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: 77.5%

9-Hydroxy-9-(2-methoxy-phenoxymethyl)-2,12-dioxo-3-oxa-6-aza-tricyclo[6.3.1.01,5]dodecane-6-carboxylic acid benzyl ester (98689-09-9) → 9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.01,5]dodecane-2,12-dione (98689-10-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 3h; under 760 Torr;

DOI:10.1021/jo00223a001

Reference yield:

2(2-methoxyphenoxy)ethanale (18167-91-4) → 9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.01,5]dodecane-2,12-dione (98689-10-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Mg / 1.) THF, from 10 to 15 deg C, 2 h, 2.) THF, RT, 30 min

2: 59 percent / Jones reagent / acetone / 0.08 h / 0 °C

3: 79.5 percent / t-BuOK / 2-methyl-propan-2-ol; benzene / 2 h / Ambient temperature

4: 77.5 percent / H₂ / 5percent Pd/C / acetic acid / 3 h / 760 Torr

With jones reagent; potassium tert-butylate; hydrogen; magnesium; palladium on activated charcoal; In acetic acid; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jo00223a001

Reference yield:

methyl 1,4,5,6-tetrahydro-2-methyl-4-oxo-3-pyridinecarboxylate (68185-61-5) → 9-Hydroxy-9-(2-methoxy-phenoxymethyl)-3-oxa-6-aza-tricyclo[6.3.1.01,5]dodecane-2,12-dione (98689-10-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) t-BuOK / 1.) DMF, t-BuOH, RT, 3.5 h, 2.) DMF, t-BuOH, RT, 1 h

2: N-bromosuccinimide, pyridine / benzene / 0.5 h / 80 - 85 °C / Irradiation

3: dimethylformamide / 13 h / Ambient temperature

4: 70 percent / p-toluenesulfonic acid / methanol / 6.5 h / Heating

5: 1.) NaBH₄, 2.) benzaldehyde / 1.) THF, pyridine, -15 deg C, 0.5 h, 2.) THF, pyridine, RT, 10 min

6: 79.5 percent / t-BuOK / 2-methyl-propan-2-ol; benzene / 2 h / Ambient temperature

7: 77.5 percent / H₂ / 5percent Pd/C / acetic acid / 3 h / 760 Torr

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; potassium tert-butylate; hydrogen; benzaldehyde; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/jo00223a001

upstream raw materials:

9-Hydroxy-9-(2-methoxy-phenoxymethyl)-2,12-dioxo-3-oxa-6-aza-tricyclo[6.3.1.0^1,5]dodecane-6-carboxylic acid benzyl ester

2(2-methoxyphenoxy)ethanale

methyl 1,4,5,6-tetrahydro-2-methyl-4-oxo-3-pyridinecarboxylate

(2-methoxyphenoxy)methyl vinyl ketone

Downstream raw materials:

6a-Hydroxy-7-(2-methoxy-phenoxy)-octahydro-furo[3,4-j]isoquinoline-1,8-dione

7-(2-Methoxy-phenoxy)-3a,4,5,6,9,10-hexahydro-3H-furo[3,4-j]isoquinoline-1,8-dione

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