tert-Butanol → 5-hydroxymethyl-5-hydroxy-1-(4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1291650Notes

Reaction equation

HRID 1291650 reaction equation
[CH2:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1.C(O)(C)(C)C.[OH2:36].[OH2:37].C[N+]([O-])(C)C.S([O-])(O)=O.[Na+]>[Os](=O)(=O)(=O)=O.N1C=CC=CC=1.O>[OH:36][CH2:1][C:2]1([OH:37])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 198430Trimethylamine oxide dihydrateHCID 196080415-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineHCID 23665763Sodium Bisulfite

Product 1

HCID 196079655-hydroxymethyl-5-hydroxy-1-(4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineYield 84.4%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To 5-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.60 g) are added successively t-butyl alcohol (6.0 ml), water (1.2 ml), pyridine (0.3 ml), osmium tetroxide (1.2 mg) and trimethylamine N-oxide dihydrate (0.22 g), and the mixture is refluxed with stirring for 2.5 hours. After cooling, to the reaction solution is added 20% aqueous sodium hydrogen-sulfite solution (10 ml), and the mixture is stirred at room temperature for 1.5 hour. The reaction solution is extracted with a mixture of ethyl acetate/tetrahydrofuran (1:1). The extract is washed successively with diluted hydrochloric acid and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is recrystallized from ethyl acetate/n-hexane to give 5-hydroxymethyl-5-hydroxy-1-(4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.55 g) as white powder, m.p. 136°-140° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling, to the reaction solution
  3. stirringthe mixture is stirred at room temperature for 1.5 hour
  4. extractionThe reaction solution is extracted with a mixture of ethyl acetate/tetrahydrofuran (1:1)
  5. washThe extract is washed successively with diluted hydrochloric acid and saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-9bbd47fa7fd346d6ab8600cc76f0198e
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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