Potassium Carbonate → 3-tert-Butoxycarbonyl-7-chloro-6-hydroxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1013098Notes

Reaction equation

HRID 1013098 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[OH:19].[C:20](=[O:23])([O-])[O-:21].[K+].[K+]>CO.O.C(Cl)Cl>[C:4]([O:21][C:20]([N:8]1[CH2:9][CH2:10][C:4]2[C:3]([OH:19])=[C:2]([Cl:1])[CH:18]=[CH:17][C:5]=2[CH2:6][CH2:7]1)=[O:23])([CH3:10])([CH3:5])[CH3:3]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 58757109HCID 58757109, compound

Product 1

HCID 574477413-tert-Butoxycarbonyl-7-chloro-6-hydroxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 209.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 7-chloro-3-(2,2,2-trifluoroacetyl)-6-hydroxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (2.0 g, 6.80 mmol) in methanol (100 mL). Add potassium carbonate (14.08 g, 102 mmol) in water (50 mL) slowly. Stir the reaction at RT for 2 h, add tert-butoxycarbonyl anhydride (1.59 g, 7.48 mmol) in DCM (70 mL) and stir vigorously for 17 h. Concentrate the organic layer, wash the aqueous layer with DCM (3×50 mL), combine the organic layers, dry (MgSO4) and concentrate to give the title compound (2.12 g, 100%).

Workup

  1. customthe reaction at RT for 2 h
  2. stirringstir vigorously for 17 h
  3. concentrationConcentrate the organic layer
  4. washwash the aqueous layer with DCM (3×50 mL)
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-55bce5d701c8484dba43bb3143f2f178
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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