HCID 22676748, compound → HCID 22676760, compound

HRID 1006259Notes

Reaction equation

HRID 1006259 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)[C:14]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:13]2[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:34]=1)[CH:8]=C>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[CH:41]1([CH2:40][O:39][C:35]2[CH:34]=[C:33]([C:13]3[C:12]4[C:16](=[CH:8][CH:7]=[C:10]([CH2:18][CH:17]=[O:2])[CH:11]=4)[N:15]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=4)[C:14]=3[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:38]=[CH:37][CH:36]=2)[CH2:43][CH2:42]1

Participants

6

Reactant 2

HCID 22676748HCID 22676748, compoundHCID 23667635Sodium periodate

Product 1

HCID 22676760HCID 22676760, compoundYield 47.3%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (430 mg, 2.0 mmol) and osmium tetroxide (2.5 wt % solution in tert-butanol, 0.50 mL, 0.05 mmol) were added to a stirred solution of ethyl 5-allyl-3-[3-(cyclopropylmethoxy)phenyl]-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 132, 385 mg, 0.777 mmol) in tetrahydrofuran (10 mL) and water (1 mL). The reaction was stirred for 18 h and then diluted with water (100 mL). The product was extracted with ethyl acetate (3×50 mL) and then the combined organic extracts were washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 15% ethyl acetate/hexane gave 183 mg (47%) of product containing impurities. The material was used in the next reaction without further purification. Mass spectroscopy gave MH+=498.1 (exact mass calc'd for C31H31NO5=497.22).

Workup

  1. extractionThe product was extracted with ethyl acetate (3×50 mL)
  2. washthe combined organic extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ab94d0531bc44d6b19c245d1d42155a
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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