Maleic Acid → (+)-(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol maleate

HRID 1363683Notes

Reaction equation

HRID 1363683 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][N:10]([CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1)[CH3:11]>C(OCC)(=O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:11][N:10]([CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1)[CH3:9]

Participants

4

Reactant 2

HCID 444266Maleic Acid2×HCID 9813414Faxeladol

Product 1

HCID 16042847(+)-(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol maleateYield 97.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
55 °C

Procedure

8.92 g of maleic acid are dissolved at 55° C. in a glass flask in 120 ml of ethyl acetate. In another glass flask 17.96 g of (+)-(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol are likewise dissolved at 55° C. at room temperature in 108 ml of ethyl acetate and slowly added dropwise within 30 minutes to the solution of maleic acid. After the addition of approx. half, a white, voluminous, finely crystalline solid precipitates out. The suspension is stirred for a further 3 hours at 55° C. once addition is complete. It is then left to cool by itself to room temperature and stirred again overnight. The precipitate is filtered out and washed once with 20 ml of ethyl acetate and dried by having air drawn through it (5 minutes). 26.26 g (97.7% of theoretical) of (+) -(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol maleate are obtained as crystalline form A (according to the X-ray diffraction pattern). DSC analysis reveals two peaks at 166.03 and 177.03° C.

Workup

  1. additionAfter the addition of approx. half
  2. customa white, voluminous, finely crystalline solid precipitates out
  3. additiononce addition
  4. waitIt is then left
  5. temperatureto cool by itself to room temperature
  6. stirringstirred again overnight
  7. filtrationThe precipitate is filtered out
  8. washwashed once with 20 ml of ethyl acetate
  9. customdried
  10. customdrawn through it (5 minutes)

Sources & evidence

ORD record
ord-babe92721a4244989fac6296754aa5f5
Source dataset
uspto-grants-2011_02
Patent number
US07884247B2

Reaction notes

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