Toluene → HCID 69300175, compound

HRID 2252379Notes

Reaction equation

HRID 2252379 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:26]([CH2:27][CH:28]4[CH2:30][CH2:29]4)[CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][C@H:19]4[C@H:18]([N:31]1[CH:39]([OH:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=O)[CH2:17][CH2:16][C@@:15]35[OH:42])C1C=CC=CC=1.[C:43]([CH:47]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:45][CH3:46])=[O:44].C(=O)([O-])O.[Na+].[C:72]1([CH3:78])[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1>>[CH2:78]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:26]([CH2:27][CH:28]4[CH2:29][CH2:30]4)[CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][C@H:19]4[C@H:18]([N:31]1[CH:32]([CH2:47][C:43]([O:45][CH3:46])=[O:44])[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:39]1=[O:40])[CH2:17][CH2:16][C@@:15]35[OH:42])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 516892Sodium BicarbonateHCID 69299942HCID 69299942, compound

Product 1

HCID 69300175HCID 69300175, compound

Procedure

In 10 mL of toluene, 200 mg (0.35 mmol) of 2-(3-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-morphinan-6β-yl)-3-hydroxy-2,3-dihydro-isoindol-1-one obtained in Example 26-1 was dissolved, and 147 mg (0.43 mmol) of (carbomethoxymethylene)triphenylphosphorane was added thereto, followed by heating the mixture to reflux for 15 hours. Thereafter, aqueous saturated sodium hydrogen carbonate solution was added to the reaction mixture, 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 the captioned compound as 33 mg of low polarity component and 38 mg of high polarity component (yields: 15% and 17%, respectively).

Workup

  1. temperatureby heating the mixture
  2. temperatureto reflux for 15 hours
  3. extractionthe resulting mixture was extracted with chloroform
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customThe obtained crude product
  9. customwas purified by silica gel column chromatography
  10. customto obtain the captioned compound as 33 mg of low polarity component and 38 mg of high polarity component (
  11. customyields

Sources & evidence

ORD record
ord-0eec986228a140d58e745e228223cedd
Source dataset
uspto-grants-2008_01
Patent number
US07320984B2

Reaction notes

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