Dicyclohexylcarbodiimide → HCID 15384845, compound

HRID 1858346Notes

Reaction equation

HRID 1858346 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.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH2:30][C:31](O)=[O:32].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:31](=[O:32])[CH2:30][C:26]2[S:25][CH:29]=[CH:28][CH:27]=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 159702-Thiopheneacetic acidHCID 10860472HCID 10860472, compound

Product 1

HCID 15384845HCID 15384845, compoundYield 76.1%

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 (1.98 g, 6 mmol) and thiophene-2-acetic acid (0.853 g, 6 mmol) are dissolved in CH2Cl2 (30 ml) at 25° C. Then N,N'-dicyclohexylcarbodiimide (1.24 g, 6 mmol) and 4-dimethylaminopyridine (0.73 g, 6 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 off and washed with CH2Cl2 (20 ml). The combined organic phase is washed with water (2×10 ml), dried (Na2SO4), filtered and evaporated down using a Rotavapor. The residue thus formed is purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1). The residue is freed from residual solvent in a high vacuum in order to obtain 4,5α-epoxy-3-methoxymethoxy-17-methyl-6α-((2-thienyl)-acetyloxy)-morphinan-7-ene (2.07 g, 76.1%) as a colourless foam.

Workup

  1. filtrationthe precipitate is filtered off
  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. customevaporated down
  7. customThe residue thus formed
  8. customis purified by flash chromatography (silica gel; mobile phase: CH2Cl2 :MeOH=9:1)

Sources & evidence

ORD record
ord-3d086cec476447d79e5e8e5e78f6d921
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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