Boron tribromide → (-)-5,6,7,8-Tetrahydro-6-[(2-phenoxyethyl)propylamino]-1-naphthalenol

HRID 327588Notes

Reaction equation

HRID 327588 reaction equation
B(Br)(Br)Br.[CH2:5]([N:8]([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[O:28]C)[CH2:19]1)[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH3:7]>ClCCl.C(Cl)(Cl)Cl>[O:11]([CH2:10][CH2:9][N:8]([CH2:5][CH2:6][CH3:7])[CH:18]1[CH2:27][CH2:26][C:25]2[C:24]([OH:28])=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 152288502-[N-n-propyl,N-2-(phenyloxy)ethylamino]-5-methoxytetralin

Product 1

HCID 15228851(-)-5,6,7,8-Tetrahydro-6-[(2-phenoxyethyl)propylamino]-1-naphthalenol

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.0M Boron tribromide in dichloromethane in 20ML chloroform was added dropwise the product of Example 1 (80 mg, .236 mmol) in chloroform and stirred at room temperature of 15 min. After workup, the crude mixture was subjected to flash chromatography (Silica: 8.2 pet ether/EtOAc). The product showed characteristic peaks at: NMR (300 MHz, CDCl3) δ 7.3-6.6(m, 8H), 4.0(t, 2H), 3.1-2.5(m,9H), 2.1(m,1H), 1.7-1.4 (m, 3H), 0.9(t, 3H).

Sources & evidence

ORD record
ord-30f0bb66efc84bb7ad15852c62078217
Source dataset
uspto-grants-1993_12
Patent number
US05274003

Reaction notes

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