Benzyl Alcohol → 1-benzyloxycarbonylmethyl-3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

HRID 1488956Notes

Reaction equation

HRID 1488956 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]([O:16][C:17]([CH3:20])(C)C)=[O:15])[C:3]1=[O:21].O.[C:23]1(C)[CH:28]=[CH:27]C(S(O)(=O)=O)=[CH:25][CH:24]=1.C(O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]([O:16][CH2:17][C:20]2[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=2)=[O:15])[C:3]1=[O:21]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 36741653-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-t-butyl acetate

Product 1

HCID 132434981-benzyloxycarbonylmethyl-3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-oneYield 69.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.5 g of tert-butyl 3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (see Example 1I) for preparation), 8.25 g of p-toluenesulfonic acid hydrate and 20.1 ml of benzyl alcohol were added to 174 ml of toluene. The reaction mixture was boiled with a water trap for 4 hours, during which a precipitate which originally separated out slowly dissolved. The toluene was then stripped off under reduced pressure, and the remaining residue was stirred with methyl tert-butyl ether and then filtered out. The resulting solid residue was dissolved in dichloromethane, and the solution was made alkaline by adding aqueous sodium carbonate solution while cooling in ice. The dichloromethane phase was then separated, washed with water, dried over sodium sulfate and evaporated. The resulting crude product was recrystallized from methyl tert-butyl ether for purification. 8.2 g of benzyl 3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate were obtained with a melting point of 105° to 107° C.

Workup

  1. customa precipitate which originally separated out slowly
  2. dissolutiondissolved
  3. filtrationfiltered out
  4. dissolutionThe resulting solid residue was dissolved in dichloromethane
  5. additionby adding aqueous sodium carbonate solution
  6. temperaturewhile cooling in ice
  7. customThe dichloromethane phase was then separated
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customThe resulting crude product was recrystallized from methyl tert-butyl ether for purification

Sources & evidence

ORD record
ord-44f406269f654ebc914e0d13fe177c27
Source dataset
uspto-grants-1997_10
Patent number
US05677297

Reaction notes

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