(2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester
CAS No.:102327-23-1
Molecular Formula:C₂₇H₃₂N₂O₆
Molecular Weight:480.561
Hs Code.:

Synonyms:(2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

There total 6 articles about (2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-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: 87.0%

: 3970-21-6
2-Methoxyethoxymethyl chloride

: 102327-15-1
(2S,3R,5R)-3-Acetyl-5-hydroxy-2-(1H-indol-3-yl)-piperidine-1-carboxylic acid benzyl ester

: 102327-23-1
(2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 15h; Ambient temperature;
DOI:10.1016/S0040-4020(01)96582-2

Reference yield:

: 55676-25-0
3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

: 102327-23-1
(2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 2.) 70percent NaAl(MeOCH₂CH₂O)2H₂ / 1.) THF, toluene, -70 deg C, 30 min, 2.) THF,toluene, -70 deg C, 30 min

2: 1.) O₂, 2.) SnCl₂ / 1.) methylene blue, CH₂Cl₂, -60 deg C, 30 min, irradiation, 2.) CH₂Cl₂, EtOAc, -60 deg C, 10 min, then -5 deg C, 2 h

3: 93 percent / 10percent HCl / methanol / 0.17 h / Ambient temperature

4: 70 percent / H₂ / PtO₂ / 1,2-dimethoxy-ethane / 3 h

5: 87 percent / iso-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

With hydrogenchloride; hydrogen; oxygen; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tin(ll) chloride; platinum(IV) oxide; In methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1016/S0040-4020(01)96582-2

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 102327-23-1
(2S,3R,5R)-3-Acetyl-2-(1H-indol-3-yl)-5-(2-methoxy-ethoxymethoxy)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 2.) 70percent NaAl(MeOCH₂CH₂O)2H₂ / 1.) THF, toluene, -70 deg C, 30 min, 2.) THF,toluene, -70 deg C, 30 min

2: 1.) O₂, 2.) SnCl₂ / 1.) methylene blue, CH₂Cl₂, -60 deg C, 30 min, irradiation, 2.) CH₂Cl₂, EtOAc, -60 deg C, 10 min, then -5 deg C, 2 h

3: 93 percent / 10percent HCl / methanol / 0.17 h / Ambient temperature

4: 70 percent / H₂ / PtO₂ / 1,2-dimethoxy-ethane / 3 h

5: 87 percent / iso-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

With hydrogenchloride; hydrogen; oxygen; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tin(ll) chloride; platinum(IV) oxide; In methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1016/S0040-4020(01)96582-2