Imidazole → HCID 67155121, compound

HRID 1044679Notes

Reaction equation

HRID 1044679 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[CH:10]([CH:24]3[O:28][CH2:27][CH2:26][O:25]3)[CH2:9][CH2:8][C@@:7]4([OH:29])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.N1C=CN=C1.[CH:35]([Si:38]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])Cl)([CH3:37])[CH3:36].O>C(Cl)Cl>[CH:35]([Si:38]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[O:20][C:15]1[CH:16]=[CH:17][C:18]2[CH2:19][C@H:6]3[N:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)[CH2:23][CH2:22][C@:12]45[C:13]=2[C:14]=1[O:21][C@H:11]4[CH:10]([CH:24]1[O:25][CH2:26][CH2:27][O:28]1)[CH2:9][CH2:8][C@@:7]35[OH:29])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 67155001HCID 67155001, compound

Product 1

HCID 67155121HCID 67155121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17-(cyclopropylmethyl)-4,5a-epoxy-3,14-dihydroxy-6-(1,3-dioxolan-2-yl)morphinan (3.85 g, 10 mmol) was dissolved in 20 ml of methylene chloride, then imidazole (0.68 g, 10 mmol) and triisopropylchlorosilane (1.92 g, 10 mmol) were added with stirring. The whole system was refluxed to react for 4 hours. After the reaction was complete, water was added for extraction and then extracted with methylene chloride for 3 times. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated for crystallization to afford a white solid.

Workup

  1. temperatureThe whole system was refluxed
  2. customto react for 4 hours
  3. extractionextracted with methylene chloride for 3 times
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated for crystallization
  7. customto afford a white solid

Sources & evidence

ORD record
ord-5fe67a7ef7414173af4617b7df04dd40
Source dataset
uspto-grants-2013_10
Patent number
US08563721B2

Reaction notes

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