Imidazole → HCID 67154960, compound

HRID 1044677Notes

Reaction equation

HRID 1044677 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.[C:35]([Si:39]([CH3:42])([CH3:41])Cl)([CH3:38])([CH3:37])[CH3:36].O>CN(C=O)C>[Si:39]([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])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 67155001HCID 67155001, compound

Product 1

HCID 67154960HCID 67154960, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17-(cyclopropylmethyl)-4,5a-epoxy-3,14-dihydroxy-6-(1,3-dioxolan-2-yl)morphinan (3.85 g, 10 mmol) was dissolved in 10 ml of DMF, then imidazole (0.68 g, 10 mmol) and tert-butyl dimethyl chlorosilane (1.5 g, 10 mmol) were added with stirring. The whole system was reacted at a temperature ranging from 20° C. to 25° C. for 40 min. After the reaction was complete, water was added to the system and the resultant mixture was extracted with diethyl ether for 3 times. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated for crystallization to afford a white solid of 4.0 g. Yield: 80%. Melting point: 107.7-109.3° C.

Workup

  1. customThe whole system was reacted at a temperature
  2. extractionthe resultant mixture was extracted with diethyl ether for 3 times
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated for crystallization
  6. customto afford a white solid of 4.0 g

Sources & evidence

ORD record
ord-05689b8a15b343189f035d249f09cc21
Source dataset
uspto-grants-2013_10
Patent number
US08563721B2

Reaction notes

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