Boron tribromide → 3-Hydroxymethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one

HRID 1594854Notes

Reaction equation

HRID 1594854 reaction equation
B(Br)(Br)Br.C[O:6][CH2:7][C:8]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=2)[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]1=[O:16]>C(Cl)Cl>[OH:6][CH2:7][C:8]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]1=[O:16]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 217062403-Methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one

Product 1

HCID 217062823-Hydroxymethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of BBr3(1.48 mL, 1.48 mmol) in CH2Cl2 was added to 3-methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one (as described in Step A above) (0.391 g, 1.35 mmol) dissolved in anh. CH2Cl2 (5 mL) at −78° C. After 24 h of stirring at RT, the reaction was quenched with H2O, extracted with CH2Cl2 (3×), dried (MgSO4), concentrated and purified using SiO2 chromatography (1-1.5% MeOH/CH2Cl2with HOAc) to give the title compound.

Workup

  1. customthe reaction was quenched with H2O
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-667f311362ed4e35aeea7dbf0a733210
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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