Dicyclohexylcarbodiimide → HCID 20638276, compound

HRID 1858351Notes

Reaction equation

HRID 1858351 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[OH:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][O:23][CH3:24])[CH:4]=[CH:5]2.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][C:36](O)=[O:37])=[CH:29][CH:28]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[O:20][C:36](=[O:37])[CH2:35][CH2:34][CH2:33][C:30]2[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=2)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][O:23][CH3:24])[CH:4]=[CH:5]2

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 782804-(4-Methoxyphenyl)butyric acidHCID 10860472HCID 10860472, compound

Product 1

HCID 20638276HCID 20638276, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

4,5α-Epoxy-3-methoxymethoxy-17-methyl-morphinan-7-en-6α-ol (2.64 g, 8 mmol) and 4-(4-methoxyphenyl)-butyric acid (1.55 g, 8 mmol) are dissolved in CH2Cl2 (30 ml) at 25° C. Then N,N'-dicyclohexylcarbodiimide (1.65 g, 8 mmol) and 4-dimethylaminopyridine (0.97 g, 8 mmol) are added to the stirred solution. After the solution has been stirred for a further 14 hours at 25° C. the precipitate is filtered oft and washed with CH2Cl2 (20 ml). The combined organic phase is washed with water (2×10 ml), dried (Na2SO4), filtered and concentrated in the Rotavapor. The residue thus obtained is purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1). The residue is freed from residual solvent under high vacuum in order to obtain 4,5α-epoxy-3-methoxymethoxy-6α-(4-(4-methoxyphenyl)-butyryloxy)-17-methyl-morphinan-7-ene (3.71 g, 91.7%)

Workup

  1. filtrationis filtered oft
  2. washwashed with CH2Cl2 (20 ml)
  3. washThe combined organic phase is washed with water (2×10 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in the Rotavapor
  7. customThe residue thus obtained
  8. customis purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1)

Sources & evidence

ORD record
ord-4d6a56cc8b894e84b5ce872c4d5d8204
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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