(1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

Base Information

Chemical Name:(1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide
CAS No.:172016-08-9
Molecular Formula:C₁₆H₂₃NO₂
Molecular Weight:261.364
Hs Code.:

Synonyms:(1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

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Chemical Property of (1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

Chemical Property:

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Technology Process of (1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

There total 5 articles about (1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide 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: 48.0%

: 75-16-1
methylmagnesium bromide

: 172016-07-8
(1R,2S)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide

: 172016-08-9
(1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

Guidance literature:: With zinc dibromide; In tetrahydrofuran; dichloromethane; toluene; at -20 ℃; for 2h;
DOI:10.1016/j.tet.2004.05.063

Reference yield:

: 140-29-4
phenylacetonitrile

: 172016-08-9
(1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaNH₂ / 1) benzene, rt, 3 h; 2) benzene, rt, 2 h

2: aq. KOH / ethanol / 15 h / Heating

3: 1.) BuLi / 1) THF, hexane, 0 - -78 deg C; 2) THF, hexane, -78 deg C, 2 h

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, -78 deg C, 1 h

5: tetrahydrofuran / 2 h / -20 °C

With potassium hydroxide; n-butyllithium; oxalyl dichloride; sodium amide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol;
DOI:10.1021/jo9518056

Reference yield:

: 96847-52-8
(1R,2S)-2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane

: 172016-08-9
(1R,2S)-2-((R)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) BuLi / 1) THF, hexane, 0 - -78 deg C; 2) THF, hexane, -78 deg C, 2 h

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, -78 deg C, 1 h

3: tetrahydrofuran / 2 h / -20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;
DOI:10.1021/jo9518056