Methanol → HCID 11359478, compound

HRID 1870252Notes

Reaction equation

HRID 1870252 reaction equation
C([O:4][CH2:5][C@H:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:9][CH2:8][CH2:7]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[OH:4][CH2:5][C@@H:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 11211019HCID 11211019, compound

Product 1

HCID 11359478HCID 11359478, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (5R)-5-acetyloxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.49 g), potassium carbonate (1.11 g) and methanol (15 ml) is stirred at room temperature for 20 minutes. The reaction solution is poured into water, and the mixture is extracted with dichloromethane. The extract is dried over sodium sulfate, and concentrated under reduced pressure to give (5S)-5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.33 g).

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe extract is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55f9c65b54c04603b4471407661c3dae
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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