N-[(1S,2S)-2-hydroxycyclohexyl]- AcetaMide

Base Information

• Chemical Name: N-[(1S,2S)-2-hydroxycyclohexyl]- AcetaMide
• CAS No.: 190848-36-3
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.213
• Mol file: 190848-36-3.mol

Synonyms:N-[(1S,2S)-2-hydroxycyclohexyl]- AcetaMide

Chemical Property of N-[(1S,2S)-2-hydroxycyclohexyl]- AcetaMide

Chemical Property:

• Boiling Point: 357.2±31.0 °C(Predicted)
• PKA: 14.71±0.40(Predicted)
• PSA: 49.33000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 0.81690

Purity/Quality:

98.5% ^*data from raw suppliers

N-[(1S,2S)-2-Hydroxycyclohexyl]acetamide, min. 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1S,2S)-2-hydroxycyclohexyl]- AcetaMide

There total 9 articles about N-[(1S,2S)-2-hydroxycyclohexyl]- AcetaMide 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: 100.0%

acetic anhydride (108-24-7) + (1S,2S)-2-hydroxycyclohexylamine hydrochloride (13374-30-6) → (1S,2S)-N-(2-hydroxycyclohexyl)acetamide (190848-36-3)

Guidance literature:

(1S,2S)-2-hydroxycyclohexylamine hydrochloride; With sodium carbonate; In acetone; at 0 ℃;

acetic anhydride; In acetone; at 0 - 20 ℃; for 3h;

DOI:10.1021/jacs.9b03844

Reference yield:

(+/-)-trans-2-aminocyclohexanol (931-16-8,6850-38-0,6982-39-4,33092-82-9,38898-70-3,74111-21-0,108267-20-5,931-15-7) → (1S,2S)-N-(2-hydroxycyclohexyl)acetamide (190848-36-3) + (1R,2R)-N-(2-hydroxycyclohexyl)acetamide (214348-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / chloroform / 8 h / 25 °C

2: Chiraldex G-TA column / 130 - 180 °C / Resolution of racemate

With dmap; In chloroform;

DOI:10.1021/jo401195c

Reference yield:

(1S,2S)-trans-2-aminocyclohexanol (931-15-7,931-16-8,6850-38-0,6982-39-4,33092-82-9,38898-70-3,74111-21-0,108267-20-5) → (1S,2S)-N-(2-hydroxycyclohexyl)acetamide (190848-36-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / ethanol; diethyl ether

2: aq. Na₂CO₃ / acetone / 1) 0 deg C --> rt, 1 h; 2) rt, 2 h

With hydrogenchloride; sodium carbonate; In diethyl ether; ethanol; acetone;

DOI:10.1021/jo970146p

upstream raw materials:

acetic anhydride

(1S,2S)-2-hydroxycyclohexylamine hydrochloride

(±)-N-((1R,2R)-2-hydroxycyclohexyl)acetamide

(1S,2S)-trans-2-aminocyclohexanol

Refernces

• 1、 Mueller, Christian E.,Zell, Daniela,Hrdina, Radim,Wende, Raffael C.,Wanka, Lukas,Schuler, Soeren M. M.,Schreiner, Peter R.. "Lipophilic oligopeptides for chemo- and enantioselective acyl transfer reactions onto alcohols". . p. 8465 - 8484. Retrieved 2013/09/24.
• 2、 Jarvo,Evans,Copeland,Miller. "Fluorescence-based screening of asymmetric acylation catalysts through parallel enantiomer analysis. Identification of a catalyst for tertiary alcohol resolution". . p. 5522 - 5527. Retrieved 2007/10/03.