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

Base Information

• Chemical Name: (1R,2S)-2-((S)-1-Hydroxy-propyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide
• CAS No.: 172016-15-8
• Molecular Formula: C₁₇H₂₅NO₂
• Molecular Weight: 275.391
• Mol file: 172016-15-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (1R,2S)-2-((S)-1-Hydroxy-propyl)-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:

(1R,2S)-1-Phenyl-2-propionyl-cyclopropanecarboxylic acid diethylamide (172016-13-6) → (1R,2S)-2-((S)-1-Hydroxy-propyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-15-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/jo9518056

Reference yield:

phenylacetonitrile (140-29-4) → (1R,2S)-2-((S)-1-Hydroxy-propyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-15-8)

Guidance literature:

Multi-step reaction with 7 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

6: PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

7: DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C

With potassium hydroxide; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; sodium amide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jo9518056

Reference yield:

2-Hydroxymethyl-1-phenyl-cyclopropanecarbonitrile (60788-55-8) → (1R,2S)-2-((S)-1-Hydroxy-propyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-15-8)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

4: tetrahydrofuran / 2 h / -20 °C

5: PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

6: DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C

With potassium hydroxide; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jo9518056

upstream raw materials:

(1R,2S)-1-Phenyl-2-propionyl-cyclopropanecarboxylic acid diethylamide

phenylacetonitrile

2-Hydroxymethyl-1-phenyl-cyclopropanecarbonitrile

(1R,2S)-2-Hydroxymethyl-1-phenyl-cyclopropanecarbonitrile

Downstream raw materials:

(1R,2S)-2-((S)-1-Azido-propyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide

(1R,2S)-2-((S)-1-Amino-propyl)-1-phenyl-cyclopropanecarboxylic acid diethylamide