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

Base Information

• Chemical Name: 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
• CAS No.: 98689-09-9
• Molecular Formula: C₂₆H₂₇NO₈
• Molecular Weight: 481.502

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 9 articles about 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 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: 79.5%

(2-methoxyphenoxy)methyl vinyl ketone (93758-01-1) + 1-<(benzyloxy)carbonyl>-2-(hydroxymethyl)-4-oxo-3-piperidinecarboxylic acid γ-lactone (98689-07-7) → 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)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; benzene; for 2h; Ambient temperature;

DOI:10.1021/jo00223a001

Reference yield:

2(2-methoxyphenoxy)ethanale (18167-91-4) → 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)

Guidance literature:

Multi-step reaction with 3 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

With jones reagent; potassium tert-butylate; magnesium; In 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)-2,12-dioxo-3-oxa-6-aza-tricyclo[6.3.1.01,5]dodecane-6-carboxylic acid benzyl ester (98689-09-9)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jo00223a001

upstream raw materials:

(2-methoxyphenoxy)methyl vinyl ketone

1-<(benzyloxy)carbonyl>-2-(hydroxymethyl)-4-oxo-3-piperidinecarboxylic acid γ-lactone

2(2-methoxyphenoxy)ethanale

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

Downstream raw materials:

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

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