Boron tribromide → 3-Ethyl-3-(3-hydroxy-phenyl)-1-(3-hydroxy-propyl)-azepan-2-one

HRID 1594904Notes

Reaction equation

HRID 1594904 reaction equation
[CH2:1]([C:3]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:10][CH2:11][CH2:12][OH:13])[C:4]1=[O:14])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:10][CH2:11][CH2:12][OH:13])[C:4]1=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21706229HCID 21706229, compound

Product 1

HCID 217062143-Ethyl-3-(3-hydroxy-phenyl)-1-(3-hydroxy-propyl)-azepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-ethyl-1-(3-hydroxy-propyl)-3-(3-methoxy-phenyl)-azepan-2-one (as described above in Step B) (0.12 g, 0.393 mmol) in CH2Cl2 (20 mL) at −78° C. was added BBr3 (1M, 0.786 mL, 0.786 mmol). The reaction mixture was stirred for 3 hr at 25° C. then quenched with H2O and extracted with EtOAc. The organic layer was separated, washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound after purification by preparative RP HPLC.

Workup

  1. customthen quenched with H2O
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-3b5e6f6023dc4e318ad1784833d1407c
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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