methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate

Base Information

Chemical Name:methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate
CAS No.:853022-56-7
Molecular Formula:C₂₂H₂₅ClN₂O₄
Molecular Weight:416.904
Hs Code.:

Synonyms:methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate

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Chemical Property of methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate

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Technology Process of methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate

There total 10 articles about methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate 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: 95.0%

: 67-56-1
methanol

: 244081-42-3
Rafabegron

: 853022-56-7
methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate

Guidance literature:: With thionyl chloride; at 0 - 20 ℃;
DOI:10.1248/cpb.53.184

Reference yield:

: 20289-27-4
7-benzyloxyindole

: 853022-56-7
methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate

Guidance literature:: Multi-step reaction with 9 steps

1: phosphorus oxychloride / 2 h / 20 °C

2: ammonium acetate; Ac₂O; AcONa / AcOH / 2 h / Heating

3: LiAlH₄ / tetrahydrofuran; diethyl ether / 5.5 h / Heating

4: 47 percent / methanol / 28 h / 20 °C

5: 48 percent / Et₃N / tetrahydrofuran / 16 h / 20 °C

6: 77 percent / H₂ / Rh/C / ethanol / 36 h / 50 - 55 °C / atmospheric pressure

7: 67 percent / K₂CO₃; KI / methanol; acetone / 3 h / Heating

8: 73 percent / aq. NaOH / ethanol / 18 h / Heating

9: 95 percent / SOCl₂ / 0 - 20 °C

With ammonium acetate; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen; sodium acetate; acetic anhydride; potassium carbonate; triethylamine; potassium iodide; trichlorophosphate; Rh on carbon; acetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; acetone; 1: Vilsmeier reaction;
DOI:10.1248/cpb.53.184

Reference yield:

: 92855-65-7
7-(benzyloxy)-1H-indole-3-carbaldehyde

: 853022-56-7
methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate

Guidance literature:: Multi-step reaction with 8 steps

1: ammonium acetate; Ac₂O; AcONa / AcOH / 2 h / Heating

2: LiAlH₄ / tetrahydrofuran; diethyl ether / 5.5 h / Heating

3: 47 percent / methanol / 28 h / 20 °C

4: 48 percent / Et₃N / tetrahydrofuran / 16 h / 20 °C

5: 77 percent / H₂ / Rh/C / ethanol / 36 h / 50 - 55 °C / atmospheric pressure

6: 67 percent / K₂CO₃; KI / methanol; acetone / 3 h / Heating

7: 73 percent / aq. NaOH / ethanol / 18 h / Heating

8: 95 percent / SOCl₂ / 0 - 20 °C

With ammonium acetate; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen; sodium acetate; acetic anhydride; potassium carbonate; triethylamine; potassium iodide; Rh on carbon; acetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; acetone;
DOI:10.1248/cpb.53.184