Water → HCID 67155029, compound

HRID 1044678Notes

Reaction equation

HRID 1044678 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.C(N(CC)CC)C.[C:37]([Si:41]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)Cl)([CH3:40])([CH3:39])[CH3:38].O>C1COCC1>[Si: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])([C:37]([CH3:40])([CH3:39])[CH3:38])([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 67155001HCID 67155001, compound

Product 1

HCID 67155029HCID 67155029, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 THF, then triethylamine (1.01 g, 10 mmol) and tert-butyldiphenyl chlorosilane (2.75 g, 10 mmol) were added with stirring. The whole system was reacted at a temperature ranging from 45° C. to 50° C. for 2 hours. 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.

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

Sources & evidence

ORD record
ord-bfac5af1e6f3487d83fe3bfd73484f19
Source dataset
uspto-grants-2013_10
Patent number
US08563721B2

Reaction notes

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