(Nitromethyl)benzene → HCID 86603354, compound

HRID 2252378Notes

Reaction equation

HRID 2252378 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C@H:10]3[N:22]([CH2:23][CH:24]4[CH2:26][CH2:25]4)[CH2:21][CH2:20][C@:16]45[C:17]=2[C:18]=1[O:19][C@H:15]4[C@H:14]([N:27]1[C:31](=[O:32])[CH:30]=[CH:29][C:28]1=[O:33])[CH2:13][CH2:12][C@@:11]35[OH:34])(=[O:3])[CH3:2].[N+]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([O-])=O.C1CCN2C(=NCCC2)CC1.C(=O)([O-])O.[Na+]>C1COCC1>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C@H:10]3[N:22]([CH2:23][CH:24]4[CH2:25][CH2:26]4)[CH2:21][CH2:20][C@:16]45[C:17]=2[C:18]=1[O:19][C@H:15]4[C@H:14]([N:27]1[C:31](=[O:32])[CH2:30][C:29](=[CH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:28]1=[O:33])[CH2:13][CH2:12][C@@:11]35[OH:34])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 69321(Nitromethyl)benzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 69299187HCID 69299187, compound

Product 1

HCID 86603354HCID 86603354, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 mL of THF, 200 mg (0.43 mmol) of N-(3-acetoxy-17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-morphinan-6β-yl)-maleimide obtained in Example 21-1 was dissolved, and 85 mg (0.62 mmol) of nitromethylbenzene and 66 mg (0.43 mmol) of DBU were added, followed by stirring the mixture at room temperature for 1 hour. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution was added, and the resulting mixture was extracted with chloroform. Organic layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography to obtain 196 mg (yield: 82%) of the captioned compound.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4027406725bd41a9be7a5a637755b704
Source dataset
uspto-grants-2008_01
Patent number
US07320984B2

Reaction notes

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