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

HRID 1957102Notes

Reaction equation

HRID 1957102 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.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O.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

8

Reactant 4

HCID 244Benzyl AlcoholHCID 10340Sodium CarbonateHCID 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 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

10.5 g of tert-butyl 3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (preparation, see Example 3I), 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 for 4 hours on a water separator, during which period a precipitate which had originally separated out went slowly in solution. After that, the toluene was swept off under reduced pressure and the remaining residue was stirred with methyl tert-butyl ether and then filtered off. The solid residue which was obtained in this way was dissolved in dichloromethane and the solution was rendered alkaline by adding aqueous sodium carbonate solution while cooling with ice. After that, the dichloromethane phase was separated, washed with water, dried over sodium sulfate and evaporated. The resulting crude product was recrystallized, for purification, from methyl tert-butyl ether. 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 from 105° to 107° C.

Workup

  1. customa precipitate which had originally separated out
  2. filtrationfiltered off
  3. customThe solid residue which was obtained in this way
  4. temperaturewhile cooling with ice
  5. customAfter that, the dichloromethane phase was separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe resulting crude product was recrystallized, for purification, from methyl tert-butyl ether

Sources & evidence

ORD record
ord-60e7ff568279492d996246b1af32e302
Source dataset
uspto-grants-1998_07
Patent number
US05783573

Reaction notes

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