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tert-Butanol → 7-chloro-5-hydroxymethyl-5-hydroxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1489069
Notes
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Reaction equation

HRID 1489069 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9]CC(=C)C=2[CH:31]=1.C[N+]1([O-])CC[O:36]CC1.S([O-])(O)=O.[Na+].[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>N1C=CC=CC=1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:47][C:45]([CH2:48][OH:36])([OH:49])[C:46]=2[CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 229034667-chloro-5-methylidene-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepineHCID 23665763Sodium Bisulfite

Product 1

HCID 229035327-chloro-5-hydroxymethyl-5-hydroxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

To a solution of 7-chloro-5-methylidene-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.28 g) in t-butanol (3 ml), pyridine (0.2 ml) and water (1.2 ml) is added 4% aqueous osmium tetraoxide solution (0.2 ml), and further thereto is added 4-methylmorpholine N-oxide (0.1 g). The mixture is refluxed for 5 hours, and cooled. Saturated aqueous sodium hydrogen sulfite solution is added to the reaction mixture, and the mixture is stirred at room temperature for 30 minutes. Water is added to the reaction solution, and the mixture is extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography to give 7-chloro-5-hydroxymethyl-5-hydroxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.14 g) as colorless amorphous.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperaturecooled
  3. extractionthe mixture is extracted with a mixture of ethyl acetate and tetrahydrofuran
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-144d3a5957344ccf981bd8c7c19f83a3
Source dataset
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05677299

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes