Dimethylalumanylium chloride → HCID 66580196, compound

HRID 2368810Notes

Reaction equation

HRID 2368810 reaction equation
[F:1][C:2]([F:14])([F:13])[C@@H:3]([CH3:12])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.C([O:17][C:18]([C:20]1([CH2:27][CH2:28]OC)[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)=O)C.[Cl-].C[Al+]C>C1(C)C=CC=CC=1>[OH:26][CH:23]1[CH2:24][CH2:25][C:20]2([C:18](=[O:17])[N:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][C@H:3]([CH3:12])[C:2]([F:13])([F:14])[F:1])=[CH:10][CH:9]=3)[CH2:28][CH2:27]2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 16686359Dimethylalumanylium chlorideHCID 582299764-Hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl esterHCID 66580012HCID 66580012, compound

Product 1

HCID 66580196HCID 66580196, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-((R)-2,2,2-Trifluoro-1-methyl-ethoxy)-phenylamine (7.57 g,) was added to a solution of 4-hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester (5.0 g, obtained in example 3, step 3) in toluene (150 ml). The mixture was stirred for 10 minutes at RT. Then, dimethylaluminiumchloride (1M in hexane, 65.1 mL) was added dropwise over a period of 45 minutes. The reaction mixture was heated to reflux for 2 h and was then kept at 95° C. for 16 h. The mixture was cooled, poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The title compound was obtained as an mixture of cis and trans diastereomers as a light brown solid (5.79 g). This mixture was used without further purification. MS (m/e): 358.3 [MH+].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. waitwas then kept at 95° C. for 16 h
  4. temperatureThe mixture was cooled
  5. extractionextracted two times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6a3df6a570c641d3b6ec2ac16229740c
Source dataset
uspto-grants-2014_04
Patent number
US08703807B2

Reaction notes

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