Ethyl Acetate → HCID 59401353, compound

HRID 2060852Notes

Reaction equation

HRID 2060852 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[CH2:13][NH:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18].B(Br)(Br)Br.C([O-])(O)=O.[Na+].CCOC(C)=O>C(Cl)Cl>[CH3:18][CH:17]([CH3:19])[CH2:16][CH2:15][NH:14][CH2:13][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][CH:12]=[C:3]2[OH:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium Bicarbonate2×HCID 59401291HCID 59401291, compound

Product 1

HCID 59401353HCID 59401353, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-methoxynaphthalene-1-ylmethyl(3-methylbutyl)amine (Preparation 13) (310 mg, 1.20 mmol) in DCM (15 mL) at −78° C., was added 1M BBr3 in DCM (3.61 mL, 3.61 mmol.). The reaction mixture was stirred at −78° C. for 16 h. NaHCO3 (0.5 mL) was added and the mixture partitioned between NaHCO3 (0.25 mmol) and EtOAc (50 mL). The aqueous phase was extracted with EtOAc (2×50 mL) and the combine organic phases washed with 1M NaOH (20 mL). The aqueous phase was acidified with 1M HCl to pH 7 and extracted with EtOAc (100 mL). The organic phase was washed with brine (25 mL) and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=2.49 min; m/z (ES+)=244.1 [M+H]+.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (2×50 mL)
  2. washthe combine organic phases washed with 1M NaOH (20 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. washThe organic phase was washed with brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-cfe26e55bb2f464b88b8e5b56a974f62
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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